1-ethyl-1H-indole-3-carboxylic acid → Quinolizidin-2-ylmethyl-1-ethylindole-3-carboxylate

HRID 741560Notes

Reaction equation

HRID 741560 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.[CH2:13]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24](O)=[O:25])=[CH:16]1)[CH3:14]>>[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:24]([C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:15]([CH2:13][CH3:14])[CH:16]=1)=[O:25]

Participants

3

Reactant 2

HCID 36971601-ethyl-1H-indole-3-carboxylic acidHCID 70077295Octahydro-2H-quinolizine-2-methanol

Product 1

HCID 131719524Quinolizidin-2-ylmethyl-1-ethylindole-3-carboxylate

Procedure

eq-2-Hydroxymethylquinolizidine (N. J. Leonard et al, J. Org. Chem., 1957, 22, 1445) was reacted with the acid chloride of 1-ethylindole-3-carboxylic acid using the method of Example 1. The product was chromatographed on silica gel eluting with ethyl acetate to afford the title compound (E16) as a pale yellow oil. This was converted to its hydrochloride salt mp 168°-172° C.

Workup

  1. customThe product was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-099246b0ed5943ce926cd786410d59da
Source dataset
uspto-grants-1996_09
Patent number
US05552398

Reaction notes

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