1H-Indole-3-carbonyl chloride → Quinolizidin-2-ylmethylindole-3-carboxylate

HRID 741555Notes

Reaction equation

HRID 741555 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:12][CH2:11][N:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4]1.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22](Cl)=[O:23])=[CH:14]1>>[CH2:4]1[CH:5]2[N:10]([CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:11][CH2:12][CH:3]1[CH2:2][O:1][C:22]([C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:13][CH:14]=1)=[O:23]

Participants

3

Reactant 2

HCID 123802781H-Indole-3-carbonyl chlorideHCID 70077295Octahydro-2H-quinolizine-2-methanol

Product 1

HCID 131719520Quinolizidin-2-ylmethylindole-3-carboxylate

Procedure

The title compound was prepared from ax-2-hydroxymethylquinolizidine (D4) and indole-3-carboxylic acid chloride using the method of Example 1. The product was purified by chromatography on neutral alumina eluting with ethyl acetate, followed by crystallisation from ether/pentane, to give the title compound (E9a) as a white solid mp 156°-157° C.

Workup

  1. customThe product was purified by chromatography on neutral alumina eluting with ethyl acetate
  2. customfollowed by crystallisation from ether/pentane

Sources & evidence

ORD record
ord-eea0e5d430844394884ee1af1c97ceb5
Source dataset
uspto-grants-1996_09
Patent number
US05552398

Reaction notes

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