Triethylamine → 3-(chloromethyl)-N-(3,3-difluorocyclobutyl)benzamide

HRID 1878432Notes

Reaction equation

HRID 1878432 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].C(N(CC)CC)C.Cl.[F:20][C:21]1([F:26])[CH2:24][CH:23]([NH2:25])[CH2:22]1>ClCCl>[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:25][CH:23]1[CH2:24][C:21]([F:26])([F:20])[CH2:22]1)=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27333243-(Chloromethyl)benzoyl chlorideHCID 225009573,3-Difluorocyclobutamine hydrochloride

Product 1

HCID 668783523-(chloromethyl)-N-(3,3-difluorocyclobutyl)benzamideYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(Chloromethyl)benzoyl chloride (13.93 mmol, 2.63 g) was stirred in dichloromethane (50 ml) at 0° C. Triethylamine (41.8 mmol, 5.81 ml, 4.23 g) and 3,3-difluorocyclobutanamine hydrochloride (13.93 mmol, 2 g) were combined in dichloromethane and added dropwise. The reaction mixture was allowed to warm to room temperature and stir overnight. The reaction mixture was washed with water, dried over sodium sulfate and concentrated under vacuum to afford the title compound (3.33 g). MS (ESI) m/z 260.3 [M+H]+

Workup

  1. additionadded dropwise
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a9ecb08071a7420dbb65157065e13031
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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