Hydrochloric Acid → HCID 21960063, compound

HRID 1601529Notes

Reaction equation

HRID 1601529 reaction equation
[F:1][C:2]1[CH:38]=[CH:37][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15]/[CH:16]=[CH:17]/[CH2:18][O:19][C:20]4[CH:21]=[C:22]([C:34](=[O:36])[CH3:35])[CH:23]=[CH:24][C:25]=4[O:26]CC4C=CC=CC=4)[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[ClH:39]>C(O)(=O)C>[ClH:39].[F:1][C:2]1[CH:38]=[CH:37][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:15]/[CH:16]=[CH:17]/[CH2:18][O:19][C:20]4[CH:21]=[C:22]([C:34](=[O:36])[CH3:35])[CH:23]=[CH:24][C:25]=4[OH:26])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21960057HCID 21960057, compound

Product 1

HCID 21960063HCID 21960063, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

The mixture of (E)-1-[3-[[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-butenyl]oxy]-4-benzyloxyphenyl]ethanone (5.5 g, 10.7 mmol), acetic acid (50 ml), and hydrochloric acid (6 ml) was heated at 75° C. for 2 hours. At the end of reaction, the solvent was reduced to about 20 ml on a rotary evaporator. The solution was poured into ice water (350 ml) and extracted with dichloromethane (3×250 ml). The dichloromethane solution was washed with brine and dried over Na4SO4. A solid formed on concentration of the solvent. This was collected by filtration (3.4 g). Recrystallization from hot methanol (40 ml) gave 1.82 g of (E)-1-[3-[[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-butenyl]oxy]-4hydroxyphenyl]ethanone hydrochloride as white crystals, 37.5%, m.p.=208-210° C.

Workup

  1. customAt the end of reaction
  2. customthe solvent was reduced to about 20 ml on a rotary evaporator
  3. additionThe solution was poured into ice water (350 ml)
  4. extractionextracted with dichloromethane (3×250 ml)
  5. washThe dichloromethane solution was washed with brine
  6. dry with materialdried over Na4SO4
  7. customA solid formed on concentration of the solvent
  8. filtrationThis was collected by filtration (3.4 g)
  9. customRecrystallization from hot methanol (40 ml)

Sources & evidence

ORD record
ord-000292fa428248eb92e2412f2c755449
Source dataset
uspto-grants-1999_11
Patent number
US05977140

Reaction notes

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