1-[7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-benzyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane → 1-[7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

HRID 1380883Notes

Reaction equation

HRID 1380883 reaction equation
[CH3:1][O:2][C:3]1[C:39]([O:40][CH3:41])=[CH:38][C:6]2[CH2:7][C:8](=[O:37])[N:9]([CH2:12][CH2:13][CH2:14][N:15](CC3C=CC=CC=3)[CH:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][C:20]([O:28][CH3:29])=[C:21]([O:26][CH3:27])[CH:22]=4)[CH2:17]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[C:39]([O:40][CH3:41])=[CH:38][C:6]2[CH2:7][C:8](=[O:37])[N:9]([CH2:12][CH2:13][CH2:14][NH:15][CH:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][C:20]([O:28][CH3:29])=[C:21]([O:26][CH3:27])[CH:22]=4)[CH2:17]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

4

Reactant 1

HCID 135796501-[7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-benzyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

Product 1

HCID 135796591-[7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Here, 1-[7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-benzyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane (0.78 g, 0.0014 mol) is hydrogenated in glacial acetic acid (20 ml) in the presence of 10% palladium/charcoal (0.1 g) for 3 hours at ambient temperature under pressure (5 bar). The catalyst is removed by suction filtering, the glacial acetic acid is distilled off in vacuo, the residue is taken up in methylene chloride/saturated potassium carbonate solution, the organic phase is washed with water, dried over magnesium sulphate, evaporated again and purified over alumina (100 g), neutral, activity II, with methylene chloride and then with increasing amounts of ethanol (up to 40%). The hydrochloride is precipitated from a solution in acetone with ethereal hydrochloric acid. Yield: 0.45 g Mp: 222°-223° C.

Workup

  1. customThe catalyst is removed by suction
  2. filtrationfiltering
  3. distillationthe glacial acetic acid is distilled off in vacuo
  4. washthe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated again
  7. custompurified over alumina (100 g)
  8. customThe hydrochloride is precipitated from a solution in acetone with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-ecdb55d6932641d3b460980477c2d47a
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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