1-Phenethylamine → HCID 21501142, compound

HRID 1729775Notes

Reaction equation

HRID 1729775 reaction equation
[OH:1][CH:2]([CH2:10][CH3:11])[CH2:3][CH2:4][CH2:5][C:6](=[O:9])[CH:7]=[CH2:8].[C:12]1([CH:18]([NH2:20])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCCCCC>[C:12]1([CH:18]([NH:20][CH2:11][CH2:10][C:2]2([OH:1])[CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][CH3:8])[O:9]2)[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 74081-PhenethylamineHCID 20362369HCID 20362369, compound

Product 1

HCID 21501142HCID 21501142, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

A solution of racemic 7-hydroxy-1-nonen-3-one [21.3 g.; crude obtained as in Example 1(d)] in hexane (200 ml.) was treated for 15 hours at 25°C. with a solution of (-)-α-phenylethylamine (11.5 g.) in hexane (115 ml.). The reaction mixture was then purified by chromatography on alumina (660 g.). Elution with hexane first gave unpolar by-products. Hexane-ether-(4:1)-, (1:1), and straight ether then eluted 2-[2-(1-phenylethylamino)-ethyl]-6-ethyl-2-tetrahydropyranol obtained in solid form after evaporation of the solvents.

Workup

  1. customThe reaction mixture was then purified by chromatography on alumina (660 g.)
  2. washElution with hexane first gave unpolar by-products

Sources & evidence

ORD record
ord-c692dd78d7524766923462af8aad6d45
Source dataset
uspto-grants-1976_11
Patent number
US03989724

Reaction notes

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