Ethyl Acetate → (1-n Butyl-4-piperidyl)methyl-2,3-dihydrothiazolo[3,2-a]indole-9-Carboxylate

HRID 1458610Notes

Reaction equation

HRID 1458610 reaction equation
[S:1]1[C:5]2=[C:6]([C:13]([OH:15])=[O:14])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[N:4]2[CH2:3][CH2:2]1.C(O[CH2:20][CH3:21])(=O)C>>[CH2:5]([N:4]1[CH2:12][CH2:11][CH:20]([CH2:21][O:14][C:13]([C:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[N:4]3[CH2:3][CH2:2][S:1][C:5]=23)=[O:15])[CH2:2][CH2:3]1)[CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 195994482,3-Dihydrothiazolo[3,2-a]indole-9-carboxylic acid

Product 1

HCID 86753467(1-n Butyl-4-piperidyl)methyl-2,3-dihydrothiazolo[3,2-a]indole-9-CarboxylateYield 31%

Procedure

The title compound was prepared from 2,3-dihydrothiazolo[3,2-a]indole-9carboxylic acid (D15) using the method of Example 10. The crude product was purified by chromatography on silica gel eluting with 5% methanol/chloroform to give a yellow oil. This was passed through a plug of basic alumina eluting with ethyl acetate to afford the title compound as a pale yellow oil (31%) which was converted to its oxalate salt and was crystallised from acetone as an off-white solid mp 212°-215° C.

Workup

  1. customThe crude product was purified by chromatography on silica gel eluting with 5% methanol/chloroform
  2. customto give a yellow oil

Sources & evidence

ORD record
ord-a16819e780df4aa4a96d9770e9e4cc7e
Source dataset
uspto-grants-1998_12
Patent number
US05852014

Reaction notes

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