Triethylamine → HCID 90044194, compound

HRID 1050238Notes

Reaction equation

HRID 1050238 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:21]1([S:24](Cl)(=[O:26])=[O:25])[CH2:23][CH2:22]1>C(Cl)Cl.CN(C1C=CN=CC=1)C.[NH4+].[Cl-].O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:24]([CH:21]3[CH2:23][CH2:22]3)(=[O:26])=[O:25])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27356291-(4-Bromophenyl)piperazineHCID 2760919Cyclopropanesulfonyl chloride

Product 1

HCID 90044194HCID 90044194, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 57429219Ammonium chloride monohydrateSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-bromophenyl)piperazine (1 g, 4.15 mmol) was dissolved in DCM (40 ml) and cooled in 0° C. Then DMAP (0.051 g, 0.415 mmol), triethylamine (0.723 ml, 5.18 mmol), and cyclopropanesulfonyl chloride (0.641 g, 4.56 mmol) were added. The reaction was stirred 1 h at rt, then diluted with DCM and saturated NH4Cl/water (1:1). The aqueous phase was separated, extracted with DCM (×2) and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated to give the desired product. LC-MS: calculated for C13H17BrN2O2S 346.02 observed m/e: 346.88 (M+H)+ (Rt 1.16/2 min).

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted with DCM (×2)
  3. washthe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d9d0fd21ab4f4bc1b8f8ce48b8c1c07c
Source dataset
uspto-grants-2016_07
Patent number
US09382243B2

Reaction notes

Loading…