Ethanol → HCID 20269156, compound

HRID 485826Notes

Reaction equation

HRID 485826 reaction equation
Cl.[C:2]1([CH:8]2[C:17]3[C:12](=[C:13](Cl)[CH:14]=[CH:15][CH:16]=3)[C:11](C(=O)C)([NH2:19])[N:10]([CH3:23])[CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]([NH2:26])[CH3:25].[CH2:27]([OH:29])[CH3:28]>>[CH2:24]([NH:26][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[CH:11]([NH:19][C:27](=[O:29])[CH3:28])[N:10]([CH3:23])[CH2:9][CH:8]2[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:25]

Participants

4

Reactant 3

HCID 702EthanolHCID 6341EthylamineHCID 70491068HCID 70491068, compound

Product 1

HCID 20269156HCID 20269156, compound

Procedure

A mixture of 5.3 g (0.015 mole) of 4-phenyl-8-chloro-acetyl-amino-2-methyl-1,2,3,4-tetrahydro-isoquinoline-hydrochloride, 15 ml (10.4 g, 0.23 mole) of ethyl amine and 50 ml of ethanol is reacted in a bomb tube at 60° C. for 5 hours. The reaction mixture is evaporated, the residual oil (7.1 g) is triturated with 50 ml of water, the mixture is made alkaline by adding 30 ml of a 30% aqueous sodium hydroxide solution under stirring and cooling. The mixture is extracted ten times with 100 ml of ether each. The ether solution is dried over anhydrous sodium sulfate and evaporated. The residual oil is rubbed with petrolether. Thus 4.3 g (0.0133 mole) of crude 8-ethylamino-acetylamino-4-phenyl-2-methyl-1,2,3,4-tetrahydro-isoquinoline are obtained in the form of a yellowish-white powder.

Workup

  1. customis reacted in a bomb tube at 60° C. for 5 hours
  2. customThe reaction mixture is evaporated
  3. customthe residual oil (7.1 g) is triturated with 50 ml of water
  4. additionby adding 30 ml of a 30% aqueous sodium hydroxide solution
  5. temperaturecooling
  6. extractionThe mixture is extracted ten times with 100 ml of ether each
  7. dry with materialThe ether solution is dried over anhydrous sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-eb4c806acd284b748ed1815135d3cb9a
Source dataset
uspto-grants-1985_08
Patent number
US04537895

Reaction notes

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