1-Propyl-1H-indole-3-carboxylic acid → Quinolizidin-2-ylmethyl-1-n-propylindole-3-carboxylate

HRID 741561Notes

Reaction equation

HRID 741561 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:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([C:25](O)=[O:26])=[CH:17]1)[CH2:14][CH3:15]>>[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:25]([C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]([CH2:13][CH2:14][CH3:15])[CH:17]=1)=[O:26]

Participants

3

Reactant 2

HCID 183207551-Propyl-1H-indole-3-carboxylic acidHCID 70077295Octahydro-2H-quinolizine-2-methanol

Product 1

HCID 131719525Quinolizidin-2-ylmethyl-1-n-propylindole-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-n-propylindole-3-carboxylic acid using the method of Example 1. The product was chromatographed on silica gel eluting with ethyl acetate. The resulting yellow oil was crystallised from n-pentane to afford the title compound (E17) as a white solid mp 75°-76° C.

Workup

  1. customThe product was chromatographed on silica gel eluting with ethyl acetate
  2. customThe resulting yellow oil was crystallised from n-pentane

Sources & evidence

ORD record
ord-218eb5a1fa7643b5bb75e3f1c30a51a6
Source dataset
uspto-grants-1996_09
Patent number
US05552398

Reaction notes

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