4-(Chloromethyl)benzoyl chloride → HCID 68425818, compound

HRID 1163072Notes

Reaction equation

HRID 1163072 reaction equation
[CH3:1][N:2]([CH3:8])[CH:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[Cl:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1>C(#N)C>[ClH:9].[Cl:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([N:5]2[CH2:6][CH2:7][CH:3]([N:2]([CH3:8])[CH3:1])[CH2:4]2)=[O:16])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 701364-(Chloromethyl)benzoyl chlorideHCID 27585193-(Dimethylamino)pyrrolidine

Product 1

HCID 68425818HCID 68425818, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 3-(dimethylamino)pyrrolidine (2.5 g, 22 mmol) in acetonitrile is added to an ice cold solution of 4-(chloromethyl)benzoyl chloride (5.0 g, 26 mmol) in acetonitrile, stirred while warming to room temperature for 2 hours then concentrated in vacuo. The resultant residue is suspended in ether and filtered to give 1-(4-chloromethylbenzoyl)-3-(N,N-dimethylamino)pyrrolidine hydrochloride as a white solid identified by NMR and MS [267 m/e (M+H)].

Workup

  1. concentrationthen concentrated in vacuo
  2. filtrationfiltered

Sources & evidence

ORD record
ord-f257d8e6490341ab914b34c23f2a14b2
Source dataset
uspto-grants-2010_10
Patent number
US07820825B2

Reaction notes

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