Propionyl chloride → (3aS,7aS)-3-[1-(4-methyl-1-propanoyl-4-piperidyl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-2-one

HRID 1642502Notes

Reaction equation

HRID 1642502 reaction equation
[CH3:1][C:2]1([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C@H:18]4[CH2:19][CH2:20][CH2:21][CH2:22][C@@H:17]4[NH:16][C:15]3=[O:23])[CH2:10][CH2:9]2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:24](Cl)(=[O:27])[CH2:25][CH3:26]>>[CH3:1][C:2]1([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C@H:18]4[CH2:19][CH2:20][CH2:21][CH2:22][C@@H:17]4[NH:16][C:15]3=[O:23])[CH2:10][CH2:9]2)[CH2:7][CH2:6][N:5]([C:24](=[O:27])[CH2:25][CH3:26])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 62324Propionyl chlorideHCID 57619802(3aS,7aS)-1-[1-(4-methyl-4-piperidyl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-3H-benzoimidazol-2-one

Product 1

HCID 25221449(3aS,7aS)-3-[1-(4-methyl-1-propanoyl-4-piperidyl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-2-oneYield 51.7%

Procedure

Following the procedure used in Step H of example 14 and starting from (3aS,7aS)-3-[1-(4-methyl-4-piperidyl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-2-one (HCl salt, 1.5 g, 3.8 mmol) and propanoyl chloride (0.43 mL, 4.89 mmol), the title compound (740 mg, 51.7%) was obtained after purification by flash chromatography (4% MeOH in dichloromethane). 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 0.96 (s, 3H), 1.18 (t, 3H), 1.3-1.5 (m, 6H), 1.4-1.9 (m, 8H), 1.92-2.02 (m, 1H), 2.1-2.3 (m, 3H), 2.32-2.4 (m, 2H), 2.84-3.08 (m, 4H), 3.23-3.4 (m, 2H), 3.42-3.5 (m, 1H), 3.82-3.88 (m, 1H), 3.7-3.8 (m, 1H), 4.43 (s, 1H). MS (M+1): 377.16

Sources & evidence

ORD record
ord-32f13487e4094d699d1af5af4dab150a
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

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