Triethylamine → 1-(1-Methylcyclopropyl)-4-(2-(trifluoromethyl)phenylsulfonyl)piperazine

HRID 2356216Notes

Reaction equation

HRID 2356216 reaction equation
[CH3:1][C:2]1([N:5]2[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3]1.CCN(CC)CC.[F:18][C:19]([F:31])([F:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26](Cl)(=[O:28])=[O:27]>ClCCl>[CH3:1][C:2]1([N:5]2[CH2:10][CH2:9][N:8]([S:26]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[C:19]([F:18])([F:30])[F:31])(=[O:28])=[O:27])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 187708711-(1-Methylcyclopropyl)piperazine

Product 1

HCID 119503981-(1-Methylcyclopropyl)-4-(2-(trifluoromethyl)phenylsulfonyl)piperazineYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(1-Methylcyclopropyl)piperazine (TFA salt) (50.9 mg, 0.200 mmol) was dissolved in dichloromethane (1.0 mL) and NEt3 (0.3 mL) was added. To this mixture, 2-trifluoromethylbenzenesulfonyl chloride (73.4 mg, 0.300 mmol) was added and the reaction mixture was stirred at room temperature for 1 h. The solvent was evaporated in vacuo and the resulting crude mixture was purified by HPLC (25-40% acetonitrile in water (0.05 TFA buffer). The product containing fractions were concentrated in vacuo until only water was left, basified with NaHCO3 (sat. aq., 20 mL) and extracted with dichloromethane (3×7 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a white solid (56.6 mg, 81%). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.28-0.32 (m, 2 H), 0.39-0.44 (m, 2 H), 0.98 (s, 3 H), 2.59 (t, J=4.80 Hz, 4 H), 3.08 (m, 4 H), 7.84-7.93 (m, 2 H), 7.99-8.04 (m, 2 H); ESI-MS: m/z 349.3 (M+H)+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe resulting crude mixture was purified by HPLC (25-40% acetonitrile in water (0.05 TFA buffer)
  3. additionThe product containing fractions
  4. concentrationwere concentrated in vacuo until only water
  5. waitwas left
  6. extractionextracted with dichloromethane (3×7 mL)
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-346a8278683d4fc88ad3f42c6cdbfe42
Source dataset
uspto-grants-2010_07
Patent number
US07759339B2

Reaction notes

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