Hydrochloric Acid → HCID 18328935, compound

HRID 1249735Notes

Reaction equation

HRID 1249735 reaction equation
B.CSC.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([CH:23]3[CH2:28][CH2:27][N:26]([C:29]4[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=4)[CH2:25][CH2:24]3)=O)[CH2:17][CH2:16]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.Cl.[OH-].[Na+]>C1COCC1.O>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH:23]3[CH2:24][CH2:25][N:26]([C:29]4[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=4)[CH2:27][CH2:28]3)[CH2:19][CH2:20]2)(=[O:13])=[O:14])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10743771HCID 10743771, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 18328935HCID 18328935, compoundYield 53.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Borane-dimethylsulphide (0.5 ml; 10M) was added dropwise to a stirred suspension of 1-(4-bromophenylsulphonyl)-4-[1-(4-pyridyl)piperidin-4-ylcarbonyl]piperazine (493 mg) in THF (10 ml) at 0-5°. The mixture was stirred for 18 hours at 25°. 6M Hydrochloric acid (4 ml) was added dropwise and the mixture stirred for 1 hour, then for 0.25 hours at reflux and then for 1 hour at 20°. The mixture was basified to pH 12 with 2M sodium hydroxide. Water (5 ml) was added and the aqueous extracted with dichloromethane (2×25 ml). Combined organic phases were dried and evaporated to give a gum, Trituration with diethyl ether (2×40 ml) gave, as a colourless solid, 1-(4-bromophenylsulphonyl)-4-[1-(4-pyridyl)piperidin-4-ylmethyl]piperazine (257 mg): m.p. 179-180° C:

Workup

  1. stirringthe mixture stirred for 1 hour
  2. temperaturefor 0.25 hours at reflux
  3. waitfor 1 hour at 20°
  4. extractionthe aqueous extracted with dichloromethane (2×25 ml)
  5. customCombined organic phases were dried
  6. customevaporated
  7. customto give a gum, Trituration with diethyl ether (2×40 ml)

Sources & evidence

ORD record
ord-1758e68ef5e546cf8c82b02d46d0956f
Source dataset
uspto-grants-2002_01
Patent number
US06335341B1

Reaction notes

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