Hydrochloric Acid → HCID 10900786, compound

HRID 1721512Notes

Reaction equation

HRID 1721512 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]=[N:7][C@@H:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH3:9])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.[OH-].[Na+]>C(O)C.C(Cl)(Cl)Cl.O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C@@H:8]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[CH3:9])=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 135977980HCID 135977980, compound

Product 1

HCID 10900786HCID 10900786, compoundYield 99.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

19.0 g (0.0794 mole) of (R)-(-)-N-(p-hydroxybenzylidene)-1-(p-tolyl)ethylamine were dissolved in 200 ml of ethyl alcohol. The resulting solution was admixed with 1.50 g (0.04 mole) of sodium borohydride at room temperature, stirred at a temperature of from 25° to 30° C. for 1 hours, and then stirred at a temperature of from 55° to 60° C. for 1 hours. After the completion of the reaction, 47 ml of a 10% hydrochloric acid were added at room temperature to the reaction mixture, which was then concentrated under reduced pressure. The residue thus obtained was admixed with 100 ml of water, and thereafter neutralized or weakly alkalized with a 20% aqueous sodium hydroxide solution. Then an extraction operation was carried out three times with 100 ml of chloroform, and the chloroform layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to give 18.99 g of (R)-(+)-N-(p-hydroxybenzyl)-1-(p-tolyl)ethylamine. Yield: 99.1%. m.p. 114.5°-116° C.; α!D24 +47.5° (C 1.0, CHCl3) NMR-spectral data (δ ppm, CDCl3) 1.27 (d) 3H; 2.32 (s) 3H; 3.42 (s) 2H; 3.69 (q) 1H; 6.3-7.4 (broad) 2H; 6.5-7.5 (m) 8H

Workup

  1. stirringstirred at a temperature of from 55° to 60° C. for 1 hours
  2. additionwere added at room temperature to the reaction mixture, which
  3. concentrationwas then concentrated under reduced pressure
  4. customThe residue thus obtained
  5. washthe chloroform layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-555e9d6b700b4ccabca107fe648b7241
Source dataset
uspto-grants-1996_04
Patent number
US05510519

Reaction notes

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