Diisopropylethylamine → 2-[N-Methyl-N-((2-methyl-naphth-1-yl)-eth-2-yl)-amino-prop-3-yl]-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-one hydrochloride

HRID 2350929Notes

Reaction equation

HRID 2350929 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:17][CH3:18])=[C:10]([O:15][CH3:16])[CH:11]=2)[C:6]1=[O:19].Cl.CN[CH2:23][CH2:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[CH3:35].[CH2:36]([N:38](C(C)C)C(C)C)C>>[ClH:1].[CH3:36][N:38]([CH:4]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:17][CH3:18])=[C:10]([O:15][CH3:16])[CH:11]=2)[C:6]1=[O:19])[CH2:3][CH3:2])[CH:24]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[CH3:35])[CH3:23]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 133270272-(3-Chloropropyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-oneHCID 19847460N-methyl-2-(2-methyl-naphth-1-yl)-ethylamine hydrochloride

Product 1

HCID 178837382-[N-Methyl-N-((2-methyl-naphth-1-yl)-eth-2-yl)-amino-prop-3-yl]-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-one hydrochloride

Procedure

A mixture of 1.13 g (4 mmol) of 2-(3-chloropropyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-one, 1.04 g (4.4 mmol) of N-methyl-2-(2-methyl-naphth-1-yl)-ethylamine hydrochloride and 1.5 ml of N-ethyl-diisopropylamine is refluxed for 2 hours. The excess N-ethyl-diisopropylamine is evaporated off in vacuo and the residue remaining is dissolved in a mixture of methylene chloride and 2 molar sodium hydroxide solution. The organic phase is separated, washed with water, dried over magnesium sulphate, evaporated down in vacuo and purified over a 150 g silica gel column (0.062-0.2 mm) with methylene chloride and then with increasing amounts of ethanol (up to 5%). The hydrochloride is precipitated from a solution in acetone with ethereal hydrochloric acid and then recrystallised from acetone.

Workup

  1. temperatureis refluxed for 2 hours
  2. customThe excess N-ethyl-diisopropylamine is evaporated off in vacuo
  3. dissolutionthe residue remaining is dissolved in a mixture of methylene chloride and 2 molar sodium hydroxide solution
  4. customThe organic phase is separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated down in vacuo
  8. custompurified over a 150 g silica gel column (0.062-0.2 mm) with methylene chloride
  9. customThe hydrochloride is precipitated from a solution in acetone with ethereal hydrochloric acid
  10. customrecrystallised from acetone

Sources & evidence

ORD record
ord-5450ade77ac84ad6927ce9b332af70d6
Source dataset
uspto-grants-1989_10
Patent number
US04871735

Reaction notes

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