4-Phenylcyclohexanone → m-(Trifluoromethyl)benzamide

HRID 2225222Notes

Reaction equation

HRID 2225222 reaction equation
Cl.N[C@@H]1CC[C@H](NC(=O)C[NH:12][C:13](=[O:24])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)CC1.C1(C2CCC(=O)CC2)C=CC=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.C(Cl)Cl>[F:21][C:20]([F:22])([F:23])[C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[C:13]([NH2:12])=[O:24]

Participants

6

Reactant 4

HCID 786054-PhenylcyclohexanoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 178479272HCID 178479272, compound

Product 1

HCID 74535m-(Trifluoromethyl)benzamideYield 140.5%

Reagents, catalysts & solvents 1

HCID 21922555Acetic acid methylene chlorideSolvent

Procedure

N-(2-(cis-4-amino-cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide hydrochloride (60 mg, 0.158 mmol, 1 eq), 4-phenylcyclohexanone (28 mg, 0.158 mmol, 1 eq) and sodium triacetoxyborohydride (67 mg, 0.316 mmol, 2 eq) were stirred in 2% acetic acid/methylene chloride (10 mL) at room temperature for 20 hours. Worked up by adding saturated sodium bicarbonate (10 mL). Stirred 10 minutes then extracted 3 times with methylene chloride (10 mL). The organic layers were combined, dried (sodium sulfate) and stripped to give an oil. Purified over silica gel in 100% ethyl acetate to 4:1 methylene chloride/methanol to give N-(2-oxo-2-(cis-4-(cis- and trans-4-phenylcyclohexylamino)cyclohexylamino)ethyl)-3-(trifluoromethyl)benzamide (42 mg) as an off-white amorphous solid. MS found: (M+H)+=502.33.

Workup

  1. extractionthen extracted 3 times with methylene chloride (10 mL)
  2. dry with materialdried (sodium sulfate)
  3. customto give an oil
  4. customPurified over silica gel in 100% ethyl acetate to 4:1 methylene chloride/methanol

Sources & evidence

ORD record
ord-64bddc64fc5f450995a3bc8a88c20031
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

Loading…