Bromine → HCID 9951887, compound

HRID 2186805Notes

Reaction equation

HRID 2186805 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:24])[CH:9]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)[CH3:10])=[CH:4][CH:3]=1.[C:25]([S-:27])#[N:26].[K+].BrBr>C(O)(=O)C>[NH2:26][C:25]1[S:27][C:7]2[CH:6]=[C:5]([CH:8]([OH:24])[CH:9]([N:11]3[CH2:16][CH2:15][CH:14]([CH2:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:13][CH2:12]3)[CH3:10])[CH:4]=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 22449936HCID 22449936, compound

Product 1

HCID 9951887HCID 9951887, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of 4 g of 1-p-aminophenyl-2-(4-benzyl-piperidin-1-yl)-propan-1-ol and 4.6 g of KSCN in 35 ml of glacial acetic acid was added dropwise 3.8 g of Br2 in 10 ml of glacial acetic acid. After 5 hours, the yellow suspension was filtered and the solution was poured into 100 ml of a concentrated hydroxide ammonium solution. After extraction with ethylacetate, the organic phase was washed with brine and dried. The solvent was removed and the residue was filtered on a small of silica gel eluting with acetone/cyclohexane ¼, affording 2.2 g of the title compound, m.p. 197-200° C., [α]20D=−15.6±0.2.

Workup

  1. filtrationthe yellow suspension was filtered
  2. additionthe solution was poured into 100 ml of a concentrated hydroxide ammonium solution
  3. extractionAfter extraction with ethylacetate
  4. washthe organic phase was washed with brine
  5. customdried
  6. customThe solvent was removed
  7. filtrationthe residue was filtered on a small of silica gel eluting with acetone/cyclohexane ¼

Sources & evidence

ORD record
ord-94d1942b9c8f493e9c75451194f3c784
Source dataset
uspto-grants-2002_06
Patent number
US06407122B1

Reaction notes

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