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Triethylamine → Cyclophosphamide

HRID 659310
Notes
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Reaction equation

HRID 659310 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:9][CH2:10][Cl:11])[P:5](Cl)(Cl)=[O:6].CN[C:14]([C:18]1[CH:23]=CC=CC=1)([OH:17])CC.C([N:26](CC)CC)C>C(OCC)(=O)C>[CH2:18]1[CH2:14][O:17][P:5]([N:4]([CH2:9][CH2:10][Cl:11])[CH2:3][CH2:2][Cl:1])(=[O:6])[NH:26][CH2:23]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96271Phosphoramidic dichloride, bis(2-chloroethyl)-HCID 19933884Methylamino-1-phenyl-1-propanol

Product 1

HCID 2907Cyclophosphamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of bis(2-chloroethyl)phosphoramidic dichloride (10 mmol) in ethyl acetate (100 mL) is added dropwise to a solution of commercial 3 methylamino-1-phenyl-1-propanol (10 mmol) and triethylamine (20 mmol) in ethyl acetate (100 mL) at rt. After stirring at rt for 3 days, the salts are filtered off and the combined filtrates are concentrated under vacuum. The crude product is purified by column chromatography on silica.

Workup

  1. filtrationthe salts are filtered off
  2. concentrationthe combined filtrates are concentrated under vacuum
  3. customThe crude product is purified by column chromatography on silica

Sources & evidence

ORD record
ord-ba24910390c54d239897abdfb963ae7b
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08080536B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes