4-Hydroxybenzaldehyde → HCID 22851149, compound

HRID 1721513Notes

Reaction equation

HRID 1721513 reaction equation
[C:1]1([C@H:7]([NH2:16])[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.[BH4-].[Na+].Cl>C(O)C>[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:16][C@@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10138221(αR)-4-Methyl-α-phenylbenzeneethanamine

Product 1

HCID 22851149HCID 22851149, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

21.13 g (0.1 mole) of (R)-(-)-α-phenyl-β-p-tolylethylamine (optical purity: 100%) and 12.82 g (0.105 mole) of p-hydroxybenzaldehyde were dissolved in 750 ml of ethyl alcohol. The reaction solution thus obtained was stirred at room temperature for 3 hours, and then stirred under reflux for 1 hour. Thereafter, the reaction solution was admixed at room temperature with 1.89 g (0.05 mole) of sodium borohydride, stirred for 3 hours, and then stirred under reflux for 1 hour. The reaction mixture was admixed with 75 ml of a 10% hydrochloric acid, and then concentrated under reduced pressure to give a crude (R)-(+)-N-p-hydroxybenzyl-α-phenyl-β-p-tolylethylamine.HCl salt, which was thereafter neutralized with an aqueous sodium hydroxide solution. The resultant solution was concentrated under reduced pressure to obtain the crystals, which were then recrystallized from ethyl alcohol, so that 20.47 g of (R)-(+)-N-p-hydroxybenzyl-α-phenyl-β-p-tolylethylamine were obtained as colorless crystals. Yield: 64.5%. m.p. 129.5°-130° C.; α!D25 +21.2° (C 1.0, CHCl3) NMR-spectral data (δ ppm, CDCl3) 2.29 (s) 3H; 2.94 (d) 2H; 3.49 (d) 2H; 3.89 (t) 1H; 3.37 (s) 2H; 6.35-6.90 (m) 4H; 6.99 (s) 4H; 7.30 (s) 5H

Workup

  1. customThe reaction solution thus obtained
  2. stirringstirred
  3. temperatureunder reflux for 1 hour
  4. stirringstirred for 3 hours
  5. stirringstirred
  6. temperatureunder reflux for 1 hour
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7973c3becf6942b5b7d8de6018a30813
Source dataset
uspto-grants-1996_04
Patent number
US05510519

Reaction notes

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