Trifluoroacetic acid → Spiro[1H-indene-1,4'-piperidin]-3(2H)-one trifluoroacetamide

HRID 1735467Notes

Reaction equation

HRID 1735467 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[CH:16]([CH2:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[CH2:14]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:23][C:24]([F:29])([F:28])[C:25](O)=[O:26].C1(OC)C=CC=CC=1>ClCCl>[F:23][C:24]([F:29])([F:28])[C:25]([NH2:8])=[O:26].[NH:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[CH2:14]2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 190304391'-(t-butyloxycarbonyl)-3,4-dihydro-3-oxospiro[1H-indene-1,4'-piperidine]

Product 1

HCID 18467060Spiro[1H-indene-1,4'-piperidin]-3(2H)-one trifluoroacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the intermediate from Step A in a 1:1:0.5 mixture of trifluoroacetic acid, dichloromethane and anisole was stirred for 1 hour and then concentrated and azeotroped from toluene to give the title compound. 1H NMR (200 MHz, CDCl3): 7.81-7.70 (m,l H), 7.62-7.45 (m, 2 H), 7.22-7.15 (m, 1 H), 3.72-3.58 (m,2 H), 3.29-3.04 (m, 2 H), 2.70 (s, 2 H), 2.47 (dt, 2 H), 1.85-1.75 (m, 2 H).

Workup

  1. concentrationconcentrated
  2. customazeotroped from toluene

Sources & evidence

ORD record
ord-a7735bce80bc49159c4585f086fbdfbc
Source dataset
uspto-grants-1996_07
Patent number
US05536716

Reaction notes

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