4-[(Benzo[b]thiophene-3-yl)carbonyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester → (Benzo[b]thiophene-3-yl)(4-piperidinyl)methanone

HRID 1598776Notes

Reaction equation

HRID 1598776 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]([CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[O:7])[C:3]2[CH:21]=[CH:22][CH:23]=[CH:24][C:2]1=2>FC(F)(F)C(O)=O.C(OCC)C>[S:1]1[CH:5]=[C:4]([C:6]([CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[O:7])[C:3]2[CH:21]=[CH:22][CH:23]=[CH:24][C:2]1=2

Participants

4

Reactant 1

HCID 153374564-[(Benzo[b]thiophene-3-yl)carbonyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester

Product 1

HCID 15337457(Benzo[b]thiophene-3-yl)(4-piperidinyl)methanone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Dissolve 4-[(benzo[b]thiophene-3-yl)carbonyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester (3.75 g, 10.8 mmol) in trifluoroacetic acid (30 mL). Stir at room temperature for 30-40 minutes. Cool in an ice bath and dilute with ethyl ether (200 mL). Keep at 0° C. for 1-2 hours, collect the solid by filtration and recrystallize (methanol/ethyl ether) to give the title compound as small colorless plates; mp 195°-197° C.

Workup

  1. temperatureCool in an ice bath
  2. waitKeep at 0° C. for 1-2 hours
  3. customcollect the solid
  4. filtrationby filtration
  5. customrecrystallize (methanol/ethyl ether)

Sources & evidence

ORD record
ord-82d4a0bb0b1a403a8167de1af8795518
Source dataset
uspto-grants-1998_04
Patent number
US05739150

Reaction notes

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