Methylamine → HCID 68122595, compound

HRID 462111Notes

Reaction equation

HRID 462111 reaction equation
[Cl:1][CH2:2][C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]3[O:18][CH2:17][O:16][C:14]3=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].[CH3:19][NH2:20]>O1CCCC1.CO>[ClH:1].[CH3:19][NH:20][CH2:2][C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]3[O:18][CH2:17][O:16][C:14]3=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 6329Methylamine2×HCID 54240701HCID 54240701, compound

Product 1

HCID 68122595HCID 68122595, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

13.5 g (0.05 mole) of 3-chloroacetyl-2,3,4,5-tetrahydro-7,8-methylenedioxy-1H-3-benzazepine was dissolved in 250 ml of dry tetrahydrofuran and the solution added to approximately 150 ml of liquid methylamine at -78°. The mixture was stirred for 20 hours allowing the temperature to rise to 22° during this interval after which it was warmed on the steambath to drive out the excess methylamine. The white solid that had formed was filtered off and washed with tetrahydrofuran. Distillation of the solvent in the rotary evaporator left 18.2 g of a thick yellow syrup which was dissolved in a minimum of hot isopropanol. Chilling gave a white salt, mp 250°-252° dec. The salt was dissolved in 30 ml of hot methanol, the solution filtered and diluted with 210 ml of ethyl acetate. On standing at room temperature white crystals of the above-named product separated, mp 253°-254°(dec.).

Workup

  1. customto rise to 22° during this interval
  2. temperaturewas warmed on the steambath
  3. customThe white solid that had formed
  4. filtrationwas filtered off
  5. washwashed with tetrahydrofuran
  6. distillationDistillation of the solvent
  7. customin the rotary evaporator
  8. waitleft 18.2 g of a thick yellow syrup which
  9. dissolutionwas dissolved in a minimum of hot isopropanol
  10. temperatureChilling
  11. customgave a white salt, mp 250°-252° dec
  12. filtrationthe solution filtered
  13. additiondiluted with 210 ml of ethyl acetate
  14. customOn standing at room temperature
  15. customseparated

Sources & evidence

ORD record
ord-81109a19c08f4b28910b2d9346f3f43f
Source dataset
uspto-grants-1977_12
Patent number
US04065473

Reaction notes

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