Methanol → Methyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-1-carboxylate

HRID 2082318

Reaction equation

HRID 2082318 reaction equation
[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[CH:3]=[C:4]1[CH2:13][CH2:12][CH2:11][CH2:10][N:5]12.[C:14](Cl)(Cl)=[O:15].[CH3:18][OH:19]>C(Cl)Cl.C1(C)C=CC=CC=1>[C:1]1([C:18]([O:15][CH3:14])=[O:19])[C:2]2[CH:3]=[C:4]3[CH2:13][CH2:12][CH2:11][CH2:10][N:5]3[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6371PhosgeneHCID 108559426,7,8,9-Tetrahydropyrido[1,2-a]indole

Product 1

HCID 19778122Methyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-1-carboxylateYield 70.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

6,7,8,9-tetrahydropyrido[1,2-a]indole (1.15 g, 6.7 mmol) in methylene chloride (5 ml) was added dropwise at 0° C. to a solution of phosgene (10 mmol) in toluene (5 ml). The reaction mixture was stirred for one hour after which methanol (1 ml) was added gradually and the mixture allowed to warm to ambient temperature. The solvent was removed under reduced pressure to yield a white solid. Recrystallization from hexane afforded 1.08 g (70.3% of methyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-1-carboxylate, as white crystals, m.p. 102°-103° C. Anal. for C14H15NO2 : Calcd. C, 73.34; H, 6.59; N, 6.11. Found: C, 72.96; H, 6.61; N, 6.33.

Workup

  1. additionwas added gradually
  2. customThe solvent was removed under reduced pressure
  3. customto yield a white solid
  4. customRecrystallization from hexane

Sources & evidence

ORD record
ord-ba37bc30eb764beab3f6b6c46c68ea25
Source dataset
uspto-grants-1993_02
Patent number
US05189041

Linked notes

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