Toluene → 7-Acetyl-1'-methyl-2,3,5,6-tetrahydrospiro[furo[3,2-f]indole-3,4'-piperidine]

HRID 1870904Notes

Reaction equation

HRID 1870904 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9](Br)=[C:10]([O:13][CH2:14][C:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH:16]=3)[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C1(C)C=CC=CC=1>C1C=CC=CC=1>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]3[C:15]4([CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]4)[CH2:14][O:13][C:10]=3[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 1140TolueneHCID 186942661-Acetyl-5-bromo-6-[(1-methyl-1,2,5,6-tetrahydropyridine-4-yl)methoxy]indoline

Product 1

HCID 186942187-Acetyl-1'-methyl-2,3,5,6-tetrahydrospiro[furo[3,2-f]indole-3,4'-piperidine]

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The title compound was prepared from 1-acetyl-5-bromo-6-[(1-methyl-1,2,5,6-tetrahydropyridine-4-yl)methoxy]indoline (D65) using a similar procedure to Description 8b in WO96/19477, but with toluene at 80° C. in place of refluxing benzene. The product was obtained from the acid/base purification as a beige solid (94%).

Workup

  1. customat 80° C.

Sources & evidence

ORD record
ord-8c21cd60f6dc45f0b44584b402f5b055
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

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