Bromine → HCID 9935736, compound

HRID 2186804Notes

Reaction equation

HRID 2186804 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:33])[CH:9]([N:20]2[CH2:25][CH2:24][CH:23]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:22][CH2:21]2)[CH2:10][NH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:34]([S-:36])#[N:35].[K+].BrBr>C(O)(=O)C>[C:12]([NH:11][CH2:10][CH:9]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:22][CH2:21]1)[CH:8]([OH:33])[C:5]1[CH:4]=[CH:3][C:2]2[N:1]=[C:34]([NH2:35])[S:36][C:7]=2[CH:6]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 22449923HCID 22449923, compound

Product 1

HCID 9935736HCID 9935736, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of 5.3 g of (+) threo 1-(p-amino-phenyl)-2-(4-benzylpiperidin-1-yl)-3-benzoylaminopropan-1-ol and 4.6 g of KSCN in 100 ml of glacial acetic acid was added dropwise a solution of 1.95 g of Br2 in 25 ml of glacial acetic acid at room temperature. After stirring for 2 h., the yellow sospension was filtered and the solution was poured into 100 ml of concentrated ammonium solution. The cloudy basic solution was extracted with ethyl acetate dried and evaporated. The residue was chromatographed on silica gel elutin with ethylacetate/cyclohexane ½, providing providing 3.7 g of the title compound, m.p. 160-162° C., [α]20D=+20.3±0.5.

Workup

  1. filtrationthe yellow sospension was filtered
  2. additionthe solution was poured into 100 ml of concentrated ammonium solution
  3. extractionThe cloudy basic solution was extracted with ethyl acetate
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel elutin with ethylacetate/cyclohexane ½
  7. customproviding

Sources & evidence

ORD record
ord-2ce41c09a9764a68a29f55a021d9b3fc
Source dataset
uspto-grants-2002_06
Patent number
US06407122B1

Reaction notes

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