Ebastine → HCID 20261587, compound

HRID 465017Notes

Reaction equation

HRID 465017 reaction equation
[C:1]1([CH:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18](=[O:29])[C:19]3[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[C:30]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH:18]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([CH3:26])([CH3:27])[CH3:28])=[CH:23][CH:24]=3)[OH:29])[CH2:11][CH2:10]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 3191EbastineHCID 4311764Sodium borohydride

Product 1

HCID 20261587HCID 20261587, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-diphenylmethoxy-1[3-(4-tert-butylbenzoyl)propyl]-piperidine (4.7 g; 0.01 mol) in ethanol (80 ml), sodium borohydride (0.4 g; 0.0105 moles) was added, and the mixture was boiled under reflux for 1.5 hours. Then the solvent was removed in vacuo and the residue dissolved in methylene chloride. The resulting solution was washed with water, dried (Na2SO4) and the solvent removed in vacuo to give an oil, which was crystallized on treatment with petroleum ether (b.p. 50°-70° C.). 4-Diphenylmethoxy-α(-4-tert-butylphenyl)-1-piperidinebutanol (3.8 g; yield 80.6%) was obtained, m.p. 129°-131° C.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. customThen the solvent was removed in vacuo
  3. dissolutionthe residue dissolved in methylene chloride
  4. washThe resulting solution was washed with water
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed in vacuo
  7. customto give an oil, which
  8. customwas crystallized on treatment with petroleum ether (b.p. 50°-70° C.)

Sources & evidence

ORD record
ord-93864070461a426a9dc70b26949f4eee
Source dataset
uspto-grants-1985_10
Patent number
US04550116

Reaction notes

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