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molecular formula C7H15Cl2N2O2P B1669514 Cyclophosphamide CAS No. 50-18-0

Cyclophosphamide

Cat. No. B1669514
M. Wt: 261.08 g/mol
InChI Key: CMSMOCZEIVJLDB-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US09115160B2

Procedure details

3-aminopropanol (2.1 g, 0.028 mol) and N-methylmorpholine (12.9 eq) are placed into a three-necked flask and stirred at room temperature. After cooling the mixture in the flask, POCl3 (4.3 g, 0.028 mol) is slowly dropped into the mixture. After adding POCl3, the mixture in the flask is stirred at room temperature for 15 hours. After that, bis(2-chloroethyl)amine hydrochloride] (5 g, 0.028 mol) is added into the mixture in the flask. The mixture in the flask is heated to about 40° C. and stirred for 6 hours. (The conversion yield determined with HPLC is about 10.0%.)
Quantity
2.1 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
Quantity
4.3 g
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four

Identifiers

REACTION_CXSMILES
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].CN1CCOCC1.[O:13]=[P:14](Cl)(Cl)Cl.Cl.[Cl:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][Cl:25]>>[CH2:3]1[CH2:4][O:5][P:14]([N:22]([CH2:23][CH2:24][Cl:25])[CH2:21][CH2:20][Cl:19])(=[O:13])[NH:1][CH2:2]1 |f:3.4|

Inputs

Step One
Name
Quantity
2.1 g
Type
reactant
Smiles
NCCCO
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN1CCOCC1
Step Two
Name
Quantity
4.3 g
Type
reactant
Smiles
O=P(Cl)(Cl)Cl
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
O=P(Cl)(Cl)Cl
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Cl.ClCCNCCCl

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
stirred at room temperature
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
is slowly dropped into the mixture
STIRRING
Type
STIRRING
Details
the mixture in the flask is stirred at room temperature for 15 hours
Duration
15 h
TEMPERATURE
Type
TEMPERATURE
Details
The mixture in the flask is heated to about 40° C.
STIRRING
Type
STIRRING
Details
stirred for 6 hours
Duration
6 h
CUSTOM
Type
CUSTOM
Details
(The conversion yield

Outcomes

Product
Name
Type
Smiles
C1CNP(=O)(OC1)N(CCCl)CCCl

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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