Pyridinium chloride → rac-cis-1-[6-(6-hydroxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-3-yl)hexyl]-4,4-dimethylpiperidine-2,6-dione

HRID 1109153Notes

Reaction equation

HRID 1109153 reaction equation
C[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[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]3[C:27](=[O:28])[CH2:26][C:25]([CH3:30])([CH3:29])[CH2:24][C:23]3=[O:31])[C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>>[OH: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[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]3[C:23](=[O:31])[CH2:24][C:25]([CH3:29])([CH3:30])[CH2:26][C:27]3=[O:28])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 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-dione

Product 1

HCID 131718497rac-cis-1-[6-(6-hydroxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-3-yl)hexyl]-4,4-dimethylpiperidine-2,6-dioneYield 89%

Procedure

In an analogous manner to that described in Example 20b), from 9.2 g (21.56 mmol) of 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 using pyridine hydrochloride there were obtained 7.9 g of (89%) rac-cis-1-[6-(6-hydroxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-3-yl)hexyl]-4,4-dimethylpiperidine-2,6-dione; yellowish crystals of m.p. 98.5°-99° after crystallization from ether/hexane.

Sources & evidence

ORD record
ord-c8b00d0fe1854fadb3847c352ff4fe0d
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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