Triethylamine → N-[2-(5-cyano-2-benzyloxyphenoxy)ethyl]-4-(1-t-butoxycarbonyl-4-piperidyloxy)benzamide

HRID 2414411Notes

Reaction equation

HRID 2414411 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]#[N:10].[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([O:35][C:36]2[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][CH:37]=2)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C>CN(C=O)C>[C:9]([C:8]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:6]([CH:7]=1)[O:5][CH2:4][CH2:3][NH:2][C:40](=[O:41])[C:39]1[CH:38]=[CH:37][C:36]([O:35][CH:32]2[CH2:31][CH2:30][N:29]([C:27]([O:26][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:28])[CH2:34][CH2:33]2)=[CH:44][CH:43]=1)#[N:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27946494-{[1-(tert-Butoxycarbonyl)piperidin-4-yl]oxy}benzoic acidHCID 226451903-(2-Aminoethoxy)-4-benzyloxybenzonitrile hydrochloride

Product 1

HCID 22645130N-[2-(5-cyano-2-benzyloxyphenoxy)ethyl]-4-(1-t-butoxycarbonyl-4-piperidyloxy)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.06 g (3.50 mmol) of 3-(2-aminoethoxy)-4-benzyloxybenzonitrile hydrochloride was dissolved in 15 ml of DMF. 1.23 g (3.84 mmol) of 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoic acid, 710 mg (4.2 mmol)) of 2-chloro-1,3-dimethylimidazonium chloride and 1.45 ml (5.19 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. After the treatment with dichloromethane as the extraction solvent in an ordinary manner, the solvent was evaporated, and the obtained residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customAfter the treatment with dichloromethane as the extraction solvent in an ordinary manner, the solvent was evaporated
  2. customthe obtained residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-4cd977b5d60d4af6b66bab3b76866f2e
Source dataset
uspto-grants-2004_11
Patent number
US06812231B2

Reaction notes

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