Dimethylamine → HCID 13726356, compound

HRID 4853Notes

Reaction equation

HRID 4853 reaction equation
Cl[CH2:2][CH:3]1[CH2:9][N:8]([CH:10]([CH3:12])[CH3:11])[C:7](=[O:13])[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[N:4]1[CH3:18].[CH3:19][NH:20][CH3:21]>CO>[CH3:18][N:4]1[C:5]2[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=2[C:7](=[O:13])[N:8]([CH:10]([CH3:12])[CH3:11])[CH2:9][CH:3]1[CH2:2][N:20]([CH3:21])[CH3:19]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 137263082-chloromethyl-1,2,3,4-tetrahydro-1-methyl-4-(1-methylethyl)-5H-1,4-benzodiazepin-5-one

Product 1

HCID 13726356HCID 13726356, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5.0 g (0.02 mole) of 2-chloromethyl-1,2,3,4-tetrahydro-1-methyl-4-(1-methylethyl)-5H-1,4-benzodiazepin-5-one, and 15.0 g (0.45 mole) of dimethylamine, and 200 ml of methanol were placed in a steel bomb and heated and stirred at 100° C. for 15 hr. After concentrating in vacuo, the residue partitioned between dilute sodium hydroxide solution and chloroform. The chloroform layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue crystallized in isopropyl ether and was recrystallized twice from the same. It weighed 29.0 g (68%), m.p. 93°-95° C.

Workup

  1. temperatureheated
  2. concentrationAfter concentrating in vacuo
  3. customthe residue partitioned between dilute sodium hydroxide solution and chloroform
  4. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue crystallized in isopropyl ether
  8. customwas recrystallized twice from the same

Sources & evidence

ORD record
ord-a24b688b91924da2b3f0df85caa2c0e1
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Reaction notes

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