N-(6-bromo-hexyl)-3,3-dimethylglutarimide → rac-cis-1-[6-(6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-3-yl)-hexyl]-4,4-dimethyl-piperidine-2,6-dione

HRID 1109225Notes

Reaction equation

HRID 1109225 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][NH:11]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]1[C:28](=[O:29])[CH2:27][C:26]([CH3:31])([CH3:30])[CH2:25][C:24]1=[O:32]>>[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][N:11]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]3[C:28](=[O:29])[CH2:27][C:26]([CH3:31])([CH3:30])[CH2:25][C:24]3=[O:32])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 19021460N-(6-bromo-hexyl)-3,3-dimethylglutarimideHCID 101650127rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole

Product 1

HCID 131718496rac-cis-1-[6-(6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-3-yl)-hexyl]-4,4-dimethyl-piperidine-2,6-dioneYield 72%

Procedure

In an analogous manner to that described in Example 20a), from rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole by reaction with N-(6-bromo-hexyl)-3,3-dimethylglutarimide there was obtained rac-cis-1-[6-(6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-3-yl)-hexyl]-4,4-dimethylpiperidine-2,6-dione; m.p. of the hydrochloride 99°-101°, yellowish crystals, yield 72%.

Sources & evidence

ORD record
ord-9d38347ac71f46bc876f7d5da85bbbaf
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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