Methylamine → HCID 59701456, compound

HRID 902665Notes

Reaction equation

HRID 902665 reaction equation
[Cl:1][C:2]1[C:35]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:33]=[CH:32][C:3]=1[CH2:4][N:5]([CH2:18][CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.[CH3:40][NH2:41].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl.CC(O)=O>[Cl:1][C:2]1[C:35]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:33]=[CH:32][C:3]=1[CH2:4][N:5]([CH2:18][CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:41][CH3:40])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86598290HCID 86598290, compound

Product 1

HCID 59701456HCID 59701456, compoundYield 16.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-benzaldehyde, (0.0443 g, 0.080 mmol) in dichloromethane (1 ml) and AcOH (00.1 mL), was treated with CH3NH2 (40% solution in H2O, 0.073 mmol) at ambient temperature. To the mixture was added NaBH(OAc)3 (0.017 g, 0.080 mmol), and the reaction was stirred overnight. The reaction mixture was then concentrated, in vacuo, to an oil, which was then dissolved in DMSO and purified via reverse-phase HPLC to afford the title compound (0.007 g, 15%); MS (ES+) m/e 568 [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrated, in vacuo, to an oil, which
  2. dissolutionwas then dissolved in DMSO
  3. custompurified via reverse-phase HPLC

Sources & evidence

ORD record
ord-d5303fd6716344f6868535fea65f70bc
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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