Trifluoroacetic acid → N-methylspiro[indene-1,4'-piperidine]-3-carboxamide

HRID 2267111Notes

Reaction equation

HRID 2267111 reaction equation
FC(F)(F)C(O)=O.[CH3:8][NH:9][C:10]([C:12]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:14]2([CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)[CH:13]=1)=[O:11]>ClCCl>[CH3:8][NH:9][C:10]([C:12]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:14]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:13]=1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59600600Tert-butyl 3-(methylcarbamoyl)spiro[indene-1,4'-piperidine]-1'-carboxylate

Product 1

HCID 59600609N-methylspiro[indene-1,4'-piperidine]-3-carboxamideYield 146%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a stirred solution of tert-butyl 3-(methylcarbamoyl)spiro[indene-1,4′-piperidine]-1′-carboxylate (C5) (0.45 g, 1.30 mmol) in dichloromethane (5 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-methylspiro[indene-1,4′-piperidine]-3-carboxamide (C6) as an oil (0.46 g). LC/MS (10-90% over 3 min with 0.9% FA) m/z 243 (M+1), Rt 1.2 minutes.

Workup

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

Sources & evidence

ORD record
ord-bc7bf39fb11c4620b95a1721ebed619a
Source dataset
uspto-grants-2010_12
Patent number
US07858790B2

Reaction notes

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