p-Bromobenzenesulfonyl chloride → HCID 131721910, compound

HRID 2289532Notes

Reaction equation

HRID 2289532 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:22][CH2:21][CH:20]([C:23]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[O:24])[CH2:19]2)=[N:14][CH:13]=1.C(N(CC)CC)C>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:28]2[CH2:29][CH2:30][N:25]([C:23]([CH:20]3[CH2:21][CH2:22][N:18]([C:15]4[CH:16]=[CH:17][N:12]=[CH:13][N:14]=4)[CH2:19]3)=[O:24])[CH2:26][CH2:27]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 18697999HCID 18697999, compound

Product 1

HCID 131721910HCID 131721910, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromophenylsulphonyl chloride (129 mg) was added at ambient temperature to a stirred solution of 1-[1-(4-pyrimidinyl)pyrrolidin-3-ylcarbonyl]piperazine (130 mg) in THF (8 ml) containing triethylamine (0.14 ml). The mixture was stirred for 2 hours then evaporated. The residue was treated with water (16 ml) and dichloromethane (30 ml) added. Aqueous was separated and re-extracted with dichloromethane (20 ml). The combined organic phases were washed with saturated brine (2×10 ml), dried and evaporated. The residue was purified by chromatography on neutral alumina eluting with dichloromethane/methanol (99/1 v/v) to give, as a colourless solid, 1-(4-bromophenylsulphonyl)-4-[1-(4-pyrimidinyl)pyrollidin-3-ylcarbonyl]piperazine (134 mg), mp 94-6°;

Workup

  1. customthen evaporated
  2. additionThe residue was treated with water (16 ml) and dichloromethane (30 ml)
  3. additionadded
  4. customAqueous was separated
  5. extractionre-extracted with dichloromethane (20 ml)
  6. washThe combined organic phases were washed with saturated brine (2×10 ml)
  7. customdried
  8. customevaporated
  9. customThe residue was purified by chromatography on neutral alumina eluting with dichloromethane/methanol (99/1 v/v)

Sources & evidence

ORD record
ord-d3ecc0db95ff48d5a60c92340a164051
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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