HCID 13579648, compound → HCID 13579649, compound

HRID 1380893Notes

Reaction equation

HRID 1380893 reaction equation
[CH3:1][O:2][C:3]1[C:33]([O:34][CH3:35])=[CH:32][C:6]2[CH2:7][C:8](=[O:31])[N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:30])[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)[CH:10]=[CH:11][C:5]=2[CH:4]=1>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[C:33]([O:34][CH3:35])=[CH:32][C:6]2[CH2:7][C:8](=[O:31])[N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:30])[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 13579648HCID 13579648, compound

Product 1

HCID 13579649HCID 13579649, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Here, 1-[7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane (1.6 g, 0.0033 mol) is hydrogenated in glacial acetic acid (20 ml) in the presence of 10% palladium/charcoal (50 g) for 6 hours at 50° C. and at pressure (5 bar). The catalyst is removed by suction filtering, the glacial acetic acid is distilled off in vacuo and the residue is neutralized after the addition of water and potssium carbonate. The precipitate is suction filtered, washed with water to remove any salts and dried. The hydrochloride is precipitated from a solution in acetone using ethereal hydrohcloric acid. Yield: 1.2 g. Mp: 236°-238° C.

Workup

  1. customThe catalyst is removed by suction
  2. filtrationfiltering
  3. distillationthe glacial acetic acid is distilled off in vacuo
  4. additionafter the addition of water and potssium carbonate
  5. filtrationfiltered
  6. washwashed with water
  7. customto remove any salts
  8. customdried
  9. customThe hydrochloride is precipitated from a solution in acetone using ethereal hydrohcloric acid

Sources & evidence

ORD record
ord-28404da2cb344b98b4fbebe8b781880e
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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