Triethylamine → HCID 89760735, compound

HRID 1479166Notes

Reaction equation

HRID 1479166 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].Cl.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH:24]([CH3:25])[CH:23]2[NH2:26])=[CH:18][CH:17]=1.C(N(CC)CC)C>C1COCC1>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C@H:22]2[C@H:24]([CH3:25])[C@H:23]2[NH:26][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=2[C:2]([F:13])([F:12])[F:1])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 89760799HCID 89760799, compound

Product 1

HCID 89760735HCID 89760735, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Trifluoromethyl-benzoyl chloride (0.028 ml, 39.4 mg, 0.17 mmol) was added to a solution of racemic (1R,2R,3S)-2-(4-chlorophenyl)-3-methyl-cyclopropanamine hydrochloride (37.2 mg, 0.17 mmol), and triethylamine (43.4 mg) in THF at 0° C. with stirring, and stirred for 18 hours. The white solid of Et3NHCl was filtered off and the filtrate concentrated and chromatographed with diethyl ether/hexane to yield 20 mg of pure racemic N-[(1R,2R,3S)-2-(4-chlorophenyl)-3-methyl-cyclopropyl]-2-(trifluoromethyl)benzamide. M.p. 167-9

Workup

  1. stirringstirred for 18 hours
  2. filtrationThe white solid of Et3NHCl was filtered off
  3. concentrationthe filtrate concentrated
  4. customchromatographed with diethyl ether/hexane

Sources & evidence

ORD record
ord-41ef2a939f964b92b69ba4579bf2a99c
Source dataset
uspto-grants-2016_08
Patent number
US09408392B2

Reaction notes

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