7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide → 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide dihydrochloride

HRID 587081Notes

Reaction equation

HRID 587081 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:22][C:21]([C:28]([NH:30][C:31]4[CH:36]=[CH:35][C:34]([CH2:37][N:38]([CH3:45])[CH:39]5[CH2:44][CH2:43][O:42][CH2:41][CH2:40]5)=[CH:33][CH:32]=4)=[O:29])=[CH:20][C:19]=3[CH:46]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[ClH:47].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:47].[ClH:47].[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:22][C:21]([C:28]([NH:30][C:31]4[CH:32]=[CH:33][C:34]([CH2:37][N:38]([CH3:45])[CH:39]5[CH2:44][CH2:43][O:42][CH2:41][CH2:40]5)=[CH:35][CH:36]=4)=[O:29])=[CH:20][C:19]=3[CH:46]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 30094087-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamideHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 223290667-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (16.4 g) in ethyl acetate (1500 ml) was added 4N hydrochloric acid-ethyl acetate (25 ml) at room temperature, and the mixture was stirred for 1 hour. The precipitated crystals were collected by filtration, which was purified by recrystallization (2-propanol) to give 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide dihydrochloride (Compound 109) (8.61 g) as pale yellow crystals.

Workup

  1. filtrationThe precipitated crystals were collected by filtration, which
  2. customwas purified by recrystallization (2-propanol)

Sources & evidence

ORD record
ord-e620646b9ef14667ad6eee0396be1ddc
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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