Morpholine → 2-Chloro-1-(3-methoxyphenyl)-indole 3-carboxylic acid morpholide

HRID 26206Notes

Reaction equation

[Cl:1][C:2]1[N:3]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[C:4]2[C:9]([C:10]=1[C:11](Cl)=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[Cl:1][C:2]1[N:3]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[C:4]2[C:9]([C:10]=1[C:11]([N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

Reactant 2

HCID 8083Morpholine

HCID 53923702HCID 53923702, compound

Product 1

HCID 537399272-Chloro-1-(3-methoxyphenyl)-indole 3-carboxylic acid morpholide

Procedure

This compound was prepared from 2-chloro-1(3-methoxyphenyl)-indole-3-carboxylic acid chloride and morpholine to yield 2-chloro-1-(3-methoxyphenyl)-indole 3-carboxylic acid morpholide which was reacted with N-methyl-piperazine according to Example 42. The yield of amorphous product was 85% of the theoretical yield; the amorpheus hydrochloride had a decomposition point above 160° C.

Sources & evidence

ORD record: ord-44b1dae9499a424cbf524879c7e936d2
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04148895

Reaction notes

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