N-Methylbenzylamine → HCID 19968859, compound

HRID 976100Notes

Reaction equation

HRID 976100 reaction equation
Cl[CH2:2][CH2:3][CH:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:5]([N:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6].[CH3:20][NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:22]([N:21]([CH2:2][CH2:3][CH:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:5]([N:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])[CH3:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 81531DiisopropylethylamineHCID 152860154-Chloro-1-(hexahydro-1H-azepin-1-yl)-2-phenyl-1-butanone

Product 1

HCID 19968859HCID 19968859, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2,3,4,5,6,7-hexahydro-1-[4-chloro-2-phenylbutanoyl]-1H-azepine (10.0 g, 35.7 mmol) in acetonitrile (100 ml) was added to a solution of N-methylbenzylamine (4.03 g, 33.3 mmol) and diisopropylethylamine (4.62 g, 35.7 mmol) in acetonitrile (40 ml) and the reaction mixture stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue dissolved in water (100 ml). The aqueous phase was washed with ethyl acetate (3×50 ml) and the combined organic phases washed with brine (50 ml), water (50 ml), dried (MgSO4) and concentrated under reduced pressure. The crude oil obtained was chromatographed on alumina, eluting with hexane:ethyl acetate (2:1) to afford the title compound as an oil (6.93 g, 53%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in water (100 ml)
  3. washThe aqueous phase was washed with ethyl acetate (3×50 ml)
  4. washthe combined organic phases washed with brine (50 ml), water (50 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude oil obtained
  8. customwas chromatographed on alumina
  9. washeluting with hexane:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-8d3699bec7e54788bbd8a59fe3272bfe
Source dataset
uspto-grants-1997_03
Patent number
US05610295

Reaction notes

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