2-Chloro-5-(trifluoromethyl)benzoyl chloride → 2-Chloro-N-(2-methyl-4-phenylaminomethyl-cyclohexyl)-5-trifluoromethyl-benzamide

HRID 2391026Notes

Reaction equation

HRID 2391026 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4][CH:3]1[CH3:16].[Cl:17][C:18]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:19]=1[C:20](Cl)=[O:21]>C1COCC1>[Cl:17][C:18]1[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][C:19]=1[C:20]([NH:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4][CH:3]1[CH3:16])=[O:21]

Participants

4

Reactant 2

HCID 27781062-Chloro-5-(trifluoromethyl)benzoyl chlorideHCID 67185375(4-Amino-3-methyl-cyclohexylmethyl)-phenyl-amine

Product 1

HCID 448161392-Chloro-N-(2-methyl-4-phenylaminomethyl-cyclohexyl)-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Amino-3-methyl-cyclohexylmethyl)-phenyl-amine (113 mg, 0.52 mmol) in dry THF (5 mL) and TEA (105 mg, 1.04 mmol) is treated with 2-chloro-5-(trifluoromethyl)benzoyl chloride (139 mg, 0.57 mmol). After stirring at RT for 2 hours, the solvent is removed in vacuo and the residue is partitioned between water and DCM. The mixture is passed through a phase separator and the organic portion is concentrated in vacuo. Purification of the crude residue by chromatography on silica eluting with iso-hexane: EtOAc (9:1 increasing to 2:1) affords the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.47 (1H, d), 7.82 (1H, d), 7.73 (2H, m), 7.07 (2H, t), 6.56 (2H, d), 6.49 (1H, t), 5.55 (1H, m), 3.93 (1H, m), 2.86 (2H, m), 2.23 (1H, m), 1.88 (1H, m), 1.78 (1H, m), 1.70 (1H, m), 1.59 (2H, m), 1.31 (1H, m), 1.11 (1H, m), 0.92 (3H,d).

Workup

  1. customthe solvent is removed in vacuo
  2. customthe residue is partitioned between water and DCM
  3. concentrationthe organic portion is concentrated in vacuo
  4. customPurification of the crude residue by chromatography on silica eluting with iso-hexane: EtOAc (9:1 increasing to 2:1)

Sources & evidence

ORD record
ord-c048a166a34c4ff3bccf09b5cca8838b
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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