Triethylamine → N-[1-[2-[1-[2-(Morpholino)ethyl]cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide

HRID 1820299Notes

Reaction equation

HRID 1820299 reaction equation
C(N(CC)CC)C.[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13](Cl)=[O:14].[C:16]1([CH3:45])[CH:21]=[CH:20][C:19]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][C:31]3([CH2:37][CH2:38][N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:25][CH2:24]2)=[CH:18][CH:17]=1>C(Cl)Cl>[O:42]1[CH2:43][CH2:44][N:39]([CH2:38][CH2:37][C:31]2([CH2:30][CH2:29][N:26]3[CH2:27][CH2:28][CH:23]([N:22]([C:19]4[CH:20]=[CH:21][C:16]([CH3:45])=[CH:17][CH:18]=4)[C:13]([C:9]4[O:8][CH:12]=[CH:11][CH:10]=4)=[O:14])[CH2:24][CH2:25]3)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]2)[CH2:40][CH2:41]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 231099094-[2-[1-[2-[4-(p-Toluidino)piperidin-1-yl]ethyl]cyclohexyl]ethyl]morpholine

Product 1

HCID 11420803N-[1-[2-[1-[2-(Morpholino)ethyl]cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamideYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding triethylamine (0.21 mL, 1.50 mmol) and 2-furoyl chloride (0.10 mL, 1.00 mmol) in that order to a solution of 4-[2-[1-[2-[4-(p-toluidino)piperidin-1-yl]ethyl]cyclohexyl]ethyl]morpholine (319 mg, 0.77 mmol) in methylene chloride (5 mL) while cooling on ice, the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (20 g Merck Art 9385, chloroform:methanol=20:1-chloroform:methanol:ammonia water=10:1:0.1) to obtain the title compound as a colorless oil (283 mg) (72% yield).

Workup

  1. temperaturewhile cooling on ice
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (20 g Merck Art 9385, chloroform:methanol=20:1-chloroform:methanol:ammonia water=10:1:0.1)

Sources & evidence

ORD record
ord-830913cb8b7a4252b017b043a42bc5d7
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

Loading…