Isopropylamine → 7-(2-Hydroxy-3-isopropylaminopropoxy)-2,2-dimethyl-4-phenylchroman

HRID 838897Notes

Reaction equation

HRID 838897 reaction equation
[O:1]1[CH2:23][CH:2]1[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10][C:11]([CH3:16])([CH3:15])[O:12]2)=[CH:7][CH:6]=1.[CH:24]([NH2:27])([CH3:26])[CH3:25]>C(O)C>[OH:1][CH:2]([CH2:23][NH:27][CH:24]([CH3:26])[CH3:25])[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:10][C:11]([CH3:15])([CH3:16])[O:12]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 233307567-(2,3-Epoxypropoxy)-2,2-dimethyl-4-phenylchroman

Product 1

HCID 30464307-(2-Hydroxy-3-isopropylaminopropoxy)-2,2-dimethyl-4-phenylchromanYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-(2,3-epoxypropoxy)-2,2-dimethyl-4-phenylchroman (6.35g.), isopropylamine (16 ml) and ethanol (16 ml) was boiled under reflux for 2 days. Removal of the solvent in vacuo gave 7-(2-hydroxy-3-isopropylaminopropoxy)-2,2-dimethyl-4-phenylchroman (6.7 g., 73%) isolated as the hydrochloride salt, m.p. 171°-174° from ether-ethanol.

Workup

  1. temperatureunder reflux for 2 days
  2. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-6b74868ce28544f3910412ab8beb8f4e
Source dataset
uspto-grants-1978_06
Patent number
US04093631

Reaction notes

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