Triethylamine → HCID 13579648, compound

HRID 1380880Notes

Reaction equation

HRID 1380880 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][C:7]([O:15][CH3:16])=[C:8]([O:13][CH3:14])[CH:9]=2)[CH2:4]1.C(N(CC)CC)C.[CH3:24][O:25][C:26]1[C:41]([O:42][CH3:43])=[CH:40][C:29]2[CH2:30][C:31](=[O:39])[N:32]([CH2:35][CH2:36][CH2:37]Cl)[CH:33]=[CH:34][C:28]=2[CH:27]=1>[OH-].[Na+].C(OCC)(=O)C>[CH3:24][O:25][C:26]1[C:41]([O:42][CH3:43])=[CH:40][C:29]2[CH2:30][C:31](=[O:39])[N:32]([CH2:35][CH2:36][CH2:37][N:2]([CH3:1])[CH:3]3[CH2:12][CH2:11][C:10]4[C:5](=[CH:6][C:7]([O:15][CH3:16])=[C:8]([O:13][CH3:14])[CH:9]=4)[CH2:4]3)[CH:33]=[CH:34][C:28]=2[CH:27]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12381618HCID 12381618, compoundHCID 130925033-(3-Chloropropyl)-1,3-dihydro-7,8-dimethoxy-2H-3-benzazepin-2-one

Product 1

HCID 13579648HCID 13579648, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-methylamino-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene (1.72 g, 0.0078 mol), triethylamine (1.09 ml, 0.0078 mol) and 1-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl)-3-chloropropane (2.3 g, 0.0078 mol) is heated to a reaction temperature of 90° C. in steps within one hour and kept at this temperature for 2 hours. The initial suspension slowly changes into a clear solution and begins to precipitate in a jelly-like manner after about 30 minutes. The cooled reaction mixture is dissolved in 0.5M sodium hydroxide solution/ethyl acetate, the organic phase is washed with water, dried over magnesium sulphate, concentrated by evaporation in vacuo and purified over alumina (300 g), neutral, activity II, with methylene chloride and then with increasing quantities of ethanol (up to 20%). The hydrochloride is precipitated from a solution in acetone using ethereal hydrochloric acid. Yield: 1.39 g Mp: >125° C. (Decomp.).

Workup

  1. customto precipitate in a jelly-like manner after about 30 minutes
  2. customThe cooled reaction mixture
  3. washthe organic phase is washed with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated by evaporation in vacuo
  6. custompurified over alumina (300 g)
  7. customThe hydrochloride is precipitated from a solution in acetone using ethereal hydrochloric acid

Sources & evidence

ORD record
ord-cf0c2551ba97461b94639a562ffeb1a7
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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