Trifluoroacetic acid → N-(pentan-3-yl)spiro[indene-1,4'-piperidine]-3-carboxamide

HRID 2267116Notes

Reaction equation

HRID 2267116 reaction equation
FC(F)(F)C(O)=O.[CH3:8][CH2:9][CH:10]([NH:13][C:14]([C:16]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:18]2([CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]2)[CH:17]=1)=[O:15])[CH2:11][CH3:12]>ClCCl>[CH3:12][CH2:11][CH:10]([NH:13][C:14]([C:16]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:18]2([CH2:19][CH2:20][NH:21][CH2:22][CH2:23]2)[CH:17]=1)=[O:15])[CH2:9][CH3:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59600632Tert-butyl 3-(pentan-3-ylcarbamoyl)spiro[inden-1,4'-piperidine]-1'-carboxylate

Product 1

HCID 25012980N-(pentan-3-yl)spiro[indene-1,4'-piperidine]-3-carboxamideYield 138.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added to a stirred solution of compound (F1) (0.60 g, 1.50 mmol) in dichloromethane (10 mL) and the solution was stirred at room temperature for 1 h. The solvent was removed under reduced pressure and dried under high vacuum for 18 h to provide N-(pentan-3-yl)spiro[indene-1,4′-piperidine]-3-carboxamide (F2) as an oil (0.62 g). LC/MS (10-90% over 3 min with 0.9% FA) m/z 299 (M+1) Rt 1.9 minutes.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customdried under high vacuum for 18 h

Sources & evidence

ORD record
ord-9a516149957f4252b1361e700c3c0630
Source dataset
uspto-grants-2010_12
Patent number
US07858790B2

Reaction notes

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