Bromine → HCID 9956521, compound

HRID 2186801Notes

Reaction equation

HRID 2186801 reaction equation
[O:1]([CH2:8][CH:9]([N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:21][CH2:20]1)[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32]([S-:34])#[N:33].[K+].BrBr>C(O)(=O)C>[O:1]([CH2:8][CH:9]([N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:21][CH2:20]1)[CH:10]([OH:11])[C:12]1[CH:17]=[CH:16][C:15]2[N:18]=[C:32]([NH2:33])[S:34][C:14]=2[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 57221881HCID 57221881, compound

Product 1

HCID 9956521HCID 9956521, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of 1.5 g of (+) three 1-phenoxymethyl-1-(4-benzylpiperidin-1-yl)-2-p-aminophenyl-2-hydroxy-ethane and 1.43 g of KSCN in 20 ml of glacial acetic acid was added dropwise a solution of 0.58 g of Br2 in 5 ml of glacial acetic acid at room temperature. After stirring for 2 h., the yellow sospension was filtered and the solution was poured into 70 ml of concentrated ammonium solution. The cloudy basic solution was extracted with ethyl acetate dried and evaporated. The resulting yellow residue was chromatographed on silica gel eluting with ethylacetate/cycloexane ⅓, furnishing after crystallization from ethanol 0.9 g of the title compound, m.p. 210-214° C., [α]20D=−2.1±0.1

Workup

  1. filtrationthe yellow sospension was filtered
  2. additionthe solution was poured into 70 ml of concentrated ammonium solution
  3. extractionThe cloudy basic solution was extracted with ethyl acetate
  4. customdried
  5. customevaporated
  6. customThe resulting yellow residue was chromatographed on silica gel eluting with ethylacetate/cycloexane ⅓
  7. customfurnishing
  8. customafter crystallization from ethanol 0.9 g of the title compound, m.p. 210-214° C., [α]20D=−2.1±0.1

Sources & evidence

ORD record
ord-3260fb57357044088c8f6e529fca0363
Source dataset
uspto-grants-2002_06
Patent number
US06407122B1

Reaction notes

Loading…