Pyrrolidine → 1-(3,4-Dihydro-2-naphthyl)pyrrolidine

HRID 467068Notes

Reaction equation

HRID 467068 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][C:9](=O)[CH2:8][CH2:7]2.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>>[N:13]1([C:9]2[CH2:8][CH2:7][C:6]3[C:11]([CH:10]=2)=[CH:2][CH:3]=[CH:4][CH:5]=3)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 41361878-Bromo-1,2,3,4-tetrahydronaphthalen-2-one

Product 1

HCID 888891-(3,4-Dihydro-2-naphthyl)pyrrolidine

Procedure

When R2 in the compounds of Formula I is methyl, the methyl-substituted 8-bromo-2-tetralone can be prepared from the corresponding unsubstituted 8-bromo-2-tetralone. The 8-bromo-2-tetralone first is treated with pyrrolidine to produce the corresponding 1,2-dihydro-3-pyrrolidinyl-naphthalene. The latter, upon treatment with methyl iodide and acid hydrolysis, gives the desired 8-bromo-1-methyl-2-tetralone.

Sources & evidence

ORD record
ord-86683599ac09440d8f72f0dd349fb60a
Source dataset
uspto-grants-1992_10
Patent number
US05158956

Reaction notes

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