Methylamine → 2-Propyn-1-amine, 3-(8-chloro-1-phenyl-3H-2-benzazepin-5-yl)-, dihydrochloride

HRID 464940Notes

Reaction equation

HRID 464940 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]2[C:6]([C:17]#[C:18][CH2:19][N:20]3C(=O)C4=CC=CC=C4C3=O)=[CH:7][CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.CN>C(O)C>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:32]=[CH:31][C:5]2[C:6]([C:17]#[C:18][CH2:19][NH2:20])=[CH:7][CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 13556892HCID 13556892, compound

Product 1

HCID 30672832-Propyn-1-amine, 3-(8-chloro-1-phenyl-3H-2-benzazepin-5-yl)-, dihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5 g (11.4 mmole) of 8-chloro-5-(1-phthalimido-2-propyn-3-yl)-1-phenyl-3H-2-benzazepine, 100 ml of ethanol and 20 ml of 40% aqueous methylamine was stirred at room temperature for 1 hr, poured into ice water and extracted with ether. The ether solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to dryness. The residue was dissolved in an excess of methanolic hydrogen chloride and concentrated at reduced pressure to dryness. The residue crystallized from a mixture of ethanol and isopropanol to give a tan solid, mp 247°-248° C. Recrystallization from a mixture of ethanol and ether gave tan prisms, mp 247°-248° C.

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated at reduced pressure to dryness
  4. dissolutionThe residue was dissolved in an excess of methanolic hydrogen chloride
  5. concentrationconcentrated at reduced pressure to dryness
  6. customThe residue crystallized from a mixture of ethanol and isopropanol
  7. customto give a tan solid, mp 247°-248° C
  8. customRecrystallization
  9. additionfrom a mixture of ethanol and ether
  10. customgave tan prisms, mp 247°-248° C.

Sources & evidence

ORD record
ord-d314924821ee40619908d60dcbea0fa8
Source dataset
uspto-grants-1985_10
Patent number
US04549988

Reaction notes

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