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

HRID 2229264Notes

Reaction equation

HRID 2229264 reaction equation
Cl.[O:2]=[C:3]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:5]2([CH2:10][CH2:9][N:8](C(C(NC(=O)C(N)(C)C)CC3C4C(=CC=CC=4)NC=3)=O)[CH2:7][CH2:6]2)[CH2:4]1.[F:37][C:38]([F:43])([F:42])[C:39](O)=[O:40].C1(OC)C=CC=CC=1>ClCCl>[F:37][C:38]([F:43])([F:42])[C:39]([NH2:8])=[O:40].[NH:8]1[CH2:9][CH2:10][C:5]2([C:31]3[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:3](=[O:2])[CH2:4]2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 18467074n-[1(r,s)-[(2,3-Dihydro-3-oxospiro [1h-indene-1,4'-piperidin]1'-yl)-carbonyl]-2-(indol-3-yl)ethyl]-2-amino-2-methylpropanamide hydrochloride

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, 1H),7.62-7.45 (m, 2H), 7.22-7.15 (m, 1H), 3.72-3.58 (m, 2H), 3.29-3.04 (m, 2H), 2.70 (s, 2H), 2.47 (dt, 2H), 1.85-1.75 (m, 2H).

Workup

  1. concentrationconcentrated
  2. customazeotroped from toluene

Sources & evidence

ORD record
ord-c20e34aa5fdc4ce5a310e9186590702d
Source dataset
uspto-grants-2002_07
Patent number
US06420376B1

Reaction notes

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