Diisopropylethylamine → HCID 68549254, compound

HRID 1868098Notes

Reaction equation

HRID 1868098 reaction equation
[CH3:1][C@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:17])([F:16])[F:15])[CH2:3]1.[C:18]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)(=[O:20])[CH3:19].C(N(C(C)C)CC)(C)C>ClCCl>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:17])([F:15])[F:16])[CH2:5][CH2:6][N:7]1[S:27]([C:24]1[CH:23]=[CH:22][C:21]([C:18](=[O:20])[CH3:19])=[CH:26][CH:25]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2664184-Acetylbenzenesulfonyl chlorideHCID 57979762HCID 57979762, compound

Product 1

HCID 68549254HCID 68549254, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-3-methyl-1-(2-trifluoromethyl-phenyl)-piperazine (500 mg, 2.05 mmol) and 4-acetylbenzenesulfonyl chloride (448.23 mg, 2.05 mmol) in anhydrous dichloromethane (6 mL) was added diisopropylethylamine (0.71 mL, 4.1 mmol). The mixture was stirred at room temperature for over night. Reaction was complete as determined by TLC. The reaction mixture was purified via flash column chromatography to yield (R)-1-{4-[2-methyl-4-(2-trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-phenyl}-ethanone in 74.0% yield (646.7 mg) as a light yellow solid. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.20 (d, J=6.57 Hz, 3H) 2.67 (s, 3H) 2.75-2.83 (m, 2H) 2.98 (d, J=10.11 Hz, 1H) 3.06 (d, J=10.11 Hz, 1H) 3.33-3.43 (m, 1H) 3.76 (d, J=10.61 Hz, 1H) 4.26 (d, J=6.82 Hz, 1H) 7.23-7.30 (m, 2H) 7.52 (t, J=7.71 Hz, 1H) 7.62 (d, J=8.08 Hz, 1H) 7.89-7.99 (m, 2H) 8.07-8.14 (m, 2H).

Workup

  1. customReaction
  2. customThe reaction mixture was purified via flash column chromatography

Sources & evidence

ORD record
ord-af7160e1e4ba449db4c074b4e54a1bff
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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