Hydrochloric Acid → 4-Amino-3-(3,4-dichlorophenyl)-1-butanol

HRID 1034470

Reaction equation

HRID 1034470 reaction equation
Cl.O1CCCCC1[O:8][CH2:9][CH2:10][CH:11]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)[CH2:12][NH2:13]>CCOCC.CO>[NH2:13][CH2:12][CH:11]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)[CH2:10][CH2:9][OH:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 156708082-(3-(3,4-Dichlorophenyl)-4-aminobutyl)oxytetrahydropyran

Product 1

HCID 97946634-Amino-3-(3,4-dichlorophenyl)-1-butanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

150 ml of a saturated solution of hydrogen chloride in ether are added to a solution of 149 g of 4-(tetrahydropyran-2-yloxy)-2-(3,4-dichlorophenyl)-1-aminobutane in 700 ml of methanol. The mixture is stirred for 1/2 hour at room temperature and concentrated under vacuum and the residue is taken up in 500 ml of water and washed with ether. The aqueous phase is rendered alkaline with a solution of sodium hydroxide and extracted twice with methylene chloride. The organic phases are dried over MgSO4, filtered and concentrated under vacuum. The residue is taken up in 400 ml of isopropyl ether and the mixture is stirred for one hour at room temperature. The precipitate is filtered off and washed with ether.

Workup

  1. concentrationconcentrated under vacuum
  2. washwashed with ether
  3. extractionextracted twice with methylene chloride
  4. dry with materialThe organic phases are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. stirringthe mixture is stirred for one hour at room temperature
  8. filtrationThe precipitate is filtered off
  9. washwashed with ether

Sources & evidence

ORD record
ord-a9aef8f98ac944b3ae5a4d65aedb6e44
Source dataset
uspto-grants-1994_05
Patent number
US05317020

Linked notes

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