Hydrochloric Acid → HCID 70156073, compound

HRID 1249734Notes

Reaction equation

HRID 1249734 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27][N:26]=4)[CH2:21][CH2:20]3)=O)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH:19]3[CH2:20][CH2:21][N:22]([C:25]4[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27][N:26]=4)[CH2:23][CH2:24]3)[CH2:15][CH2:16]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18328902HCID 18328902, compound

Product 1

HCID 70156073HCID 70156073, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Bromophenylsulphonyl)-4-[1-(6-methylpyrimidin-4-yl)-4-piperidylcarbonyl]piperazine (630 mg) suspended in dry THF (10 ml) was treated with excess borane methyl sulphide complex (0.59 ml) at ambient temprature, then at 45° C. for 18 hours. 5M HCl (1.0 ml) was added and stirred for 2 hours. The reaction mixture was basified with 4M NaOH solution. then partitioned between ethylacetate and water. dried (MgSO4), and evaporated. The residue was chromatographed on Bondelut (CH2Cl2 then 1% MeOH/CH2Cl2,2% MeOH/CH2Cl2) to give 1-(4-bromophenylsulphonyl)-4-[1-(6-methylpyrimidin-4-yl)-4-piperidylmethyl]piperazine (276 mg) as a gum.

Workup

  1. additionwas treated with excess borane methyl sulphide complex (0.59 ml) at ambient temprature
  2. customthen partitioned between ethylacetate and water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was chromatographed on Bondelut (CH2Cl2

Sources & evidence

ORD record
ord-22e07ec9e0dc4015be93fb3471316091
Source dataset
uspto-grants-2002_01
Patent number
US06335341B1

Reaction notes

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