1-Methylindole-3-carboxylic acid → Quinolizidin-2-ylmethyl-1-methylindole-3-carboxylate

HRID 741559Notes

Reaction equation

HRID 741559 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.[CH3:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([C:23](O)=[O:24])=[CH:15]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:23]([C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:14]([CH3:13])[CH:15]=1)=[O:24]

Participants

3

Reactant 2

HCID 8540401-Methylindole-3-carboxylic acidHCID 70077295Octahydro-2H-quinolizine-2-methanol

Product 1

HCID 131719523Quinolizidin-2-ylmethyl-1-methylindole-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-methylindole-3-carboxylic acid using the method of Example 1. The product was chromatographed on silica gel eluting with ethyl acetate. The resulting pale yellow oil was crystallised from n-pentane to afford the title compound (E15) as a white crystalline solid mp 115°-116° C.

Workup

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

Sources & evidence

ORD record
ord-50a1fb1b1f1d47c88ee9b76c062fb496
Source dataset
uspto-grants-1996_09
Patent number
US05552398

Reaction notes

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