Triethylamine → HCID 58728057, compound

HRID 1992102Notes

Reaction equation

HRID 1992102 reaction equation
Cl.Cl.[CH3:3][C:4]1[N:8]([CH:9]2[CH2:15][CH:14]3[N:16]([CH2:17][CH2:18][C:19]4([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=5[CH3:31])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[CH:11]([CH2:12][CH2:13]3)[CH2:10]2)[C:7]2[CH:32]=[CH:33][CH:34]=[CH:35][C:6]=2[N:5]=1.C(N(CC)CC)C.[CH3:43][C:44]([CH3:49])([CH3:48])[C:45](Cl)=[O:46]>ClCCl>[CH3:43][C:44]([CH3:49])([CH3:48])[C:45]([N:22]1[CH2:21][CH2:20][C:19]([CH2:18][CH2:17][N:16]2[C@H:14]3[CH2:13][CH2:12][C@@H:11]2[CH2:10][CH:9]([N:8]2[C:7]4[CH:32]=[CH:33][CH:34]=[CH:35][C:6]=4[N:5]=[C:4]2[CH3:3])[CH2:15]3)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH2:24][CH2:23]1)=[O:46]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 68676328HCID 68676328, compound

Product 1

HCID 58728057HCID 58728057, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-methyl-1-(8-{2-[4-(2-methylphenyl)piperidin-4-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-1H-benzimidazole dihydrochloride (0.15 g, 0.31 mmol), triethylamine (0.087 mL, 0.62 mmol) and trimethylacetyl chloride (0.043 mL, 0.34 mmol) in dichloromethane (3 mL) was stirred at rt for 1 h. The reaction mixture was diluted with dichloromethane, washed with saturated sodium bicarbonate solution, dried, concentrated and purified by chromatography on silica gel eluting with 33:1 dichloromethane:methanol to give 1-((1R,5S)-8-{2-[1-(2,2-dimethylpropanoyl)-4-(2-methylphenyl)piperidin-4-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole as a white solid (0.073 g, 45%). 1H NMR (400 MHz, CDCl3) δ 7.67 (m, 1H), 7.13-7.31 (m, 7H), 4.62 (m, 1H), 3.86 (m, 2H), 3.48 (m, 2H), 3.24 (m, 2H), 2.56 (m, 6H), 2.34 (m, 4H), 10.93 (m, 8H), 1.60 (m, 4H), 1.27 (s, 9H). HRMS C34H46N4O m/z 527.3750 (M+H)Cal., 527.3749 (M+H)Obs..

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. customdried
  3. concentrationconcentrated
  4. custompurified by chromatography on silica gel eluting with 33:1 dichloromethane

Sources & evidence

ORD record
ord-7494d5f1fb15407a93719f4b28553a25
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

Loading…