N-hydroxymethyl dichloroacetamide → 1-Cyclopentyl-5-dichloroacetylaminomethylisoquinoline

HRID 1156920Notes

Reaction equation

[CH:1]1([C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O[CH2:17][NH:18][C:19](=[O:23])[CH:20]([Cl:22])[Cl:21]>>[CH:1]1([C:6]2[C:15]3[C:10](=[C:11]([CH2:17][NH:18][C:19](=[O:23])[CH:20]([Cl:22])[Cl:21])[CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Reactant 2

HCID 12832764N-hydroxymethyl dichloroacetamide

HCID 205339561-Cyclopentylisoquinoline

Product 1

HCID 128518531-Cyclopentyl-5-dichloroacetylaminomethylisoquinoline

Procedure

1-Cyclopentylisoquinoline (obtained from 1-cyano-2-benzoyl-1,2-dihydroisoquinoline and cyclopentyl bromide) and N-hydroxymethyl dichloroacetamide were reacted in the same way as in step (b) of Example 18 to obtain 1-cyclopentyl-5-dichloroacetylaminomethylisoquinoline having a melting point of 151.0° to 152.3° C. The product was successively reacted in the same way as in steps (c), (d), (e), and (f) of Example 18 to afford 1-cyclopentylisoquinoline-5-acetonitrile having a melting point of 99.4° to 100.0° C.

Sources & evidence

ORD record: ord-df30e8a6fc9b4034a50d0f24421abbb4
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04337256

Reaction notes

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