Sodium borohydride → HCID 67854747, compound

HRID 257088Notes

Reaction equation

HRID 257088 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[C:9]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][CH:21]([N:24]([CH3:33])[CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1)(=[O:11])[CH3:10].[BH4-].[Na+]>CO>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[OH:11][CH:9]([C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH2:19][CH2:20][CH:21]([N:24]([CH3:33])[CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:22][CH2:23]2)=[CH:16][CH:17]=1)[CH3:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19784367HCID 19784367, compound

Product 1

HCID 67854747HCID 67854747, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10.4 g (0.32 mol) of the product from Example 12 (as base) were dissolved in 500 ml of methanol and, at 10° C., 18.0 g (0.475 mol) of sodium borohydride were added a little at a time. The mixture was stirred at room temperature for 16 hours and then evaporated in a rotary evaporator. The residue was partitioned between methylene chloride and water, and the organic phase was dried and evaporated in a rotary evaporator. The resulting oil was crystallized as the fumarate. 16.4 g of 1-(4-(1-hydroxyethyl)phenyl)-4-(N-methyl-N-(2-phenylethyl)amino)piperidine difumarate were obtained. Melting point 124°-129° C.

Workup

  1. customevaporated in a rotary evaporator
  2. customThe residue was partitioned between methylene chloride and water
  3. customthe organic phase was dried
  4. customevaporated in a rotary evaporator
  5. customThe resulting oil was crystallized as the fumarate

Sources & evidence

ORD record
ord-1f9a38b58c594237870a9d38d237eb2d
Source dataset
uspto-grants-1993_11
Patent number
US05260318

Reaction notes

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