Ethanol → HCID 67916296, compound

HRID 1197111Notes

Reaction equation

HRID 1197111 reaction equation
[C:1]([NH:7][C:8]1[CH:9]=[CH:10][C:11]2[CH2:17][CH2:16][C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[N:13](C(=O)CCl)[C:12]=2[CH:26]=1)([O:3][CH:4]([CH3:6])C)=[O:2].[CH2:27]([OH:29])[CH3:28].[CH3:30][NH2:31]>O>[C:1]([NH:7][C:8]1[CH:9]=[C:10]([C:27](=[O:29])[CH3:28])[C:11]2[CH2:17][CH2:16][C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[N:13]([NH:31][CH:30]3[CH2:10][CH2:9][CH2:8][CH2:26][CH2:12]3)[C:12]=2[CH:26]=1)([O:3][CH2:4][CH3:6])=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 1919982HCID 1919982, compound

Product 1

HCID 67916296HCID 67916296, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
50 °C

Procedure

18 g, approximately 0.05 moles of 3-carbisopropoxyamino-5-chloroacetyl-10,11-dihydro-5H-dibenz[b,f]azepine (hereafter referred to as Startazeine 2) and 300 ml of 96% ethanol are added to a 2liter 3-neck flask. At room temperature, 100 ml of aqueous monomethylamine solution (38%=1.2 moles) are added with stirring. The reaction mixture is heated slowly by means of a water bath to 50° C., stirred for 3 hours at this temperature and then for another hour at 60° C. After cooling to 25° C.-30° C., 750 ml of cold water are added. After standing overnight, an additional 400 ml of water are added with stirring. The water-amine-alcohol mixture is decanted from the oily deposit formed and same amount of fresh water is added. After decanting the supernatant once more, the oily residue is dissolved in 80 ml of warm acetone, cleaned through a filter and induced to crystallize in the refrigerator. The yield is 11 g, or 60% of the theoretical yield. The melting point is 150° C.-152° C. The empirical formula is C21H25N3O3, and the molecular weight is 367.46.

Workup

  1. additionare added to a 2liter 3-neck flask
  2. stirringstirred for 3 hours at this temperature
  3. waitfor another hour at 60° C
  4. temperatureAfter cooling to 25° C.-30° C.
  5. stirringwith stirring
  6. customThe water-amine-alcohol mixture is decanted from the oily deposit
  7. customformed
  8. customAfter decanting the supernatant once more
  9. dissolutionthe oily residue is dissolved in 80 ml of warm acetone
  10. filtrationa filter
  11. customto crystallize in the refrigerator

Sources & evidence

ORD record
ord-b3ad5c120a3f4db184012cb1aaa6405f
Source dataset
uspto-grants-1992_05
Patent number
US05116974

Reaction notes

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