Cyclopropanecarbonyl chloride → HCID 20534453, compound

HRID 1156989Notes

Reaction equation

[C:1]1([C:7]23[CH2:15][CH2:14][CH2:13][CH:12]2[CH2:11][NH:10][CH2:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:16]1([C:19](Cl)=[O:20])[CH2:18][CH2:17]1>>[C:1]1([C:7]23[CH2:15][CH2:14][CH2:13][CH:12]2[CH2:11][N:10]([C:19]([CH:16]2[CH2:18][CH2:17]2)=[O:20])[CH2:9][CH2:8]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 77637Cyclopropanecarbonyl chloride

HCID 20534426HCID 20534426, compound

Product 1

HCID 20534453HCID 20534453, compound

Procedure

Following the procedure outlined in Example 28, 4a-phenyl-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindine was acylated with cyclopropanecarboxylic acid chloride to provide 4a-phenyl-2-cyclopropanecarbonyl-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindine. Reduction of the acylated pyrindine intermediate by reaction with lithium aluminium hydride afforded the corresponding 2-alkyl pyrindine, which when reacted with hydrobromic acid provided 4a-phenyl-2-cyclopropylmethyl-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindinium bromide. M.P. 240°-241° C.

Sources & evidence

ORD record: ord-ff98593ab83b481589349f61c1556344
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04337341

Reaction notes

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