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

HRID 609588Notes

Reaction equation

HRID 609588 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>>[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]([O:1][CH2:2][CH:3]2[CH2:12][CH2:11][N:10]3[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]3)[CH2:4]2)=[O:23])=[CH:14]1

Participants

3

Reactant 2

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

Product 1

HCID 131719520Quinolizidin-2-ylmethylindole-3-carboxylate

Procedure

eq-2-Hydroxymethylquinolizidine (N. J. Leonard et al., J. Org. Chem., 1957, 22, 1445) was reacted with indole-3-carboxylic acid chloride using the method described in Example 1 a to afford eq-quinolizidin-2-ylmethyl 1-H-indole-3-carboxylate mp 154-157° C.

Sources & evidence

ORD record
ord-8e3a402399f0436e9efede74d56438a7
Source dataset
uspto-grants-1999_12
Patent number
US05998409

Reaction notes

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