Trifluoroacetic acid → 7-Chloro-5-piperidin-4-ylmethyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427519Notes

Reaction equation

HRID 2427519 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:16]=[C:17]3[C:21](=[C:22]([Cl:24])[CH:23]=2)[C:20](=[O:25])[N:19]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=2)[CH2:18]3)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:24][C:22]1[CH:23]=[C:15]([CH2:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:16]=[C:17]2[C:21]=1[C:20](=[O:25])[N:19]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]([F:36])([F:37])[F:35])=[CH:29][CH:28]=1)[CH2:18]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 579496974-[7-Chloro-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindol-5-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 579492977-Chloro-5-piperidin-4-ylmethyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-oneYield 109.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[7-Chloro-1-oxo-2-(4-trifluoromethoxybenzyl)-2,3-dihydro-1H-isoindol-5-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester (54.90 mg, 0.102 mmol) was stirred in dichloromethane (2 mL) and trifluoroacetic acid (2 mL) overnight. The reaction mixture was quenched with sodium carbonate to pH=8-9 and the free base was extracted with dichloromethane. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated to provide the title compound (48.9 mg, 100%). 1H NMR (300 MHz, CDCl3): δ 7.39 (d, 2H), 7.18 (d, 3H), 7.06 (s, 1H), 4.77 (s, 2H), 4.61 (broad s, 1H), 4.23 (s, 2H), 3.16 (d, 2H), 2.62 (m, 4H), 1.61 (d, 3H), 1.29 (m, 2H).

Workup

  1. customThe reaction mixture was quenched with sodium carbonate to pH=8-9
  2. extractionthe free base was extracted with dichloromethane
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-05b5d966573445aaa5c9a0cd07b113b3
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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