2-Butanamine, 2-methyl- → 1-(3,4-Dichlorophenyl)-2-(tert-amylamino)ethanol hydrochloride

HRID 482288Notes

Reaction equation

HRID 482288 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:12])[CH2:10]Br)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:13][C:14]([NH2:18])([CH2:16][CH3:17])[CH3:15]>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:12])[CH2:10][NH:18][C:14]([CH2:16][CH3:17])([CH3:15])[CH3:13])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 689862-Butanamine, 2-methyl-HCID 3441362-Bromo-1-(3,4-dichlorophenyl)ethanol

Product 1

HCID 190639411-(3,4-Dichlorophenyl)-2-(tert-amylamino)ethanol hydrochlorideYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

27 g (0.1 mol) of 1-(3,4-dichlorophenyl)-2-bromoethanol are added in the cold state to a solution of 37.5 g (50 ml) (0.43 mol) of 2-methyl-2-butylamine, 100 ml of ethanol and 0.5 g of KI. After 48 hours in contact at 20° C. and 3 hours under reflux, the mixture is filtered, the filtrate is evaporated under vacuum, the residue is taken up with ether and the organic phase is washed with water. 200 ml of N HCl are added, and the product is drained and washed with 20 ml of cold water and with ether. The hydrochloride (m.p.=184°-185° C.) is obtained in a 78% yield.

Workup

  1. temperature3 hours under reflux
  2. filtrationthe mixture is filtered
  3. customthe filtrate is evaporated under vacuum
  4. washthe organic phase is washed with water
  5. addition200 ml of N HCl are added
  6. washwashed with 20 ml of cold water and with ether

Sources & evidence

ORD record
ord-1241d34b6f0e4d53bdaf40758f3b2004
Source dataset
uspto-grants-1998_08
Patent number
US05795915

Reaction notes

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