Cyclopentanone → (3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propoxy}-phenyl)-cyclopentyl-amine dihydrochloride salt

HRID 902640Notes

Reaction equation

HRID 902640 reaction equation
[ClH:1].Cl.[Cl:3][C:4]1[C:36]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:34]=[CH:33][C:5]=1[CH2:6][N:7]([CH2:19][CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=1.[C:41]1(=O)[CH2:45][CH2:44][CH2:43][CH2:42]1.C([BH3-])#N.[Na+]>C(O)C>[ClH:3].[ClH:1].[Cl:3][C:4]1[C:36]([C:37]([F:38])([F:39])[F:40])=[CH:35][CH:34]=[CH:33][C:5]=1[CH2:6][N:7]([CH2:19][CH:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([NH:18][CH:41]2[CH2:45][CH2:44][CH2:43][CH2:42]2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 86598284HCID 86598284, compound

Product 1

HCID 86598283(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propoxy}-phenyl)-cyclopentyl-amine dihydrochloride salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenylamine dihydrochloride (53 mg, 0.086 mmol) was diluted with absolute ethanol (3 mL). Next, both cyclopentanone (7.2 mg, 0.086 mmol) and sodium cyanoborohydride (19.2 mg, 0.3 mmol) were added to the solution. The reaction mixture was stirred at room temperature overnight and concentrated under a stream of argon. Water was added and the reaction mixture was extracted with ethyl acetate. The crude amine was purified by preparative HPLC chromatography (Varian Mega BondElut Si) to afford the title compound as the free base. Addition of 1 N HCl in Et2O gave the title compound as a white powder, 22 mg (42%). MS (ESI) 608 (M+H+).

Workup

  1. concentrationconcentrated under a stream of argon
  2. additionWater was added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. customThe crude amine was purified by preparative HPLC chromatography (Varian Mega BondElut Si)

Sources & evidence

ORD record
ord-0dd1fb2acd2f4ba992879019b5af0a79
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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