Triethylamine → HCID 18432745, compound

HRID 2305364Notes

Reaction equation

[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[N:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][N:24]([C:27]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[O:28])[CH2:23][CH2:22]2)=[CH:17][CH:16]=1.C(N(CC)CC)C>ClCCl>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:32]2[CH2:31][CH2:30][N:29]([C:27]([N:24]3[CH2:25][CH2:26][N:21]([C:18]4[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=4)[CH2:22][CH2:23]3)=[O:28])[CH2:34][CH2:33]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 4-trifluoromethylphenylsulphonyl chloride (6.62 g) in dichloromethane (5 mL) was added dropwise over 10 minutes to a stirred solution of 1-[1-(4-pyridyl)piperazin-4-ylcarbonyl]piperazine (5.7 g) (prepared as in Example 1) in dichloromethane (50 mL) containing triethylamine (6 mL) at 20° C. The reaction mixture was stirred for 2 hours at 20° C. The organic phase was washed with water (3×100 mL) and saturated brine solution (2×100 mL) dried and evaporated. The residue was purified by chromatography on silica gel, eluting with a mixture of dichloromethane: methanol (95:5) to give, as a sandy-coloured solid, 1-(4-trifluoromethylphenylsulphonyl)-4-[1-(4-pyridyl)piperazin-4-ylcarbonyl]piperazine (6.0 g): NMR (CDCl3): 3.08(t, 4H), 3.30-3.40 (m, 8H), 3.40-3.45(t, 4H), 6.63(d, 2H), 7.82(d, 2H), 7.90(d, 2H), 8.30(d, 2H); EI-MS m/z 484(M+H).

Workup

washThe organic phase was washed with water (3×100 mL) and saturated brine solution (2×100 mL)
customdried
customevaporated
customThe residue was purified by chromatography on silica gel
washeluting with a mixture of dichloromethane: methanol (95:5)

Sources & evidence

ORD record: ord-9d6725c46f33469aa9e0dd217a9d7a9d
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06440972B1

Reaction notes

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