Trifluoroacetic acid → HCID 22603436, compound

HRID 2307928Notes

Reaction equation

HRID 2307928 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([CH:35]=[CH:36][C:37]=1[Cl:38])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[C:14]1[C:28]([O:30]C(C)(C)C)=[O:29]>ClCCl>[Cl:8][C:9]1[CH:10]=[C:11]([CH:35]=[CH:36][C:37]=1[Cl:38])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)=[C:14]1[C:28]([OH:30])=[O:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22603403HCID 22603403, compound

Product 1

HCID 22603436HCID 22603436, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 ml) was added to a solution of t-butyl N-(3,4-dichlorobenzyl)-3-morpholinoindole-2-carboxylate (293 mg) in dichloromethane (10 ml) and the reaction stirred at ambient temperature overnight. The reaction was concentrated in vacuo and the residue purified by column chromatography using 20% ethyl acetate:iso-hexane as eluent to afford the product as a brown solid (125 mg, 30%); NMR d (CD3SOCD3) 3.10 (t, 4H), 3.83 (t, 4H), 5.36 (s, 2H), 7.01 (t, 1H), 7.12 (m, 2H), 7.46 (m, 2H), 7.58 (m, 2H), M/z(−) 404.2 (M−H+).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-47a246db671f4201b2114e18ba7f5270
Source dataset
uspto-grants-2004_12
Patent number
US06833387B1

Reaction notes

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