Triethylamine → Cyclohexanecarboxylic acid [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-amide

HRID 1827545Notes

Reaction equation

HRID 1827545 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)[CH:18]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH:37]1([C:43](Cl)=[O:44])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)[CH:18]=3)[C:43]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[O:44])=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 22137433[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-amine

Product 1

HCID 86592786Cyclohexanecarboxylic acid [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-amine (119 mg, 0.3 mmol) and triethylamine (0.125 mL, 0.90 mmol) in methylene chloride was added to a vial charged with cyclohexanecarbonyl chloride (88 mg, 0.6 mmol). The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added until the solution was basic and the layers were separated. The aqueous layer was washed with methylene chloride. The organic layers were combined and evaporated under a stream of nitrogen to give the title compound of Step A.

Workup

  1. customthe layers were separated
  2. washThe aqueous layer was washed with methylene chloride
  3. customevaporated under a stream of nitrogen

Sources & evidence

ORD record
ord-290729691326454cafe1eb7b8e5cfd3e
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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