Morpholine → HCID 13726355, compound

HRID 4852Notes

Reaction equation

HRID 4852 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH2:11][CH3:12])[C:8](=[O:13])[C:7]2[CH:14]=[CH:15][CH:16]=[CH:17][C:6]=2[N:5]1[CH3:18].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>>[CH2:11]([N:9]1[C:8](=[O:13])[C:7]2[CH:14]=[CH:15][CH:16]=[CH:17][C:6]=2[N:5]([CH3:18])[CH:4]([CH2:3][CH2:2][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH2:10]1)[CH3:12]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 13726307HCID 13726307, compound

Product 1

HCID 13726355HCID 13726355, compoundYield 61%

Procedure

A solution of 30 g (0.112 mole) of 2-(2-chloroethyl)-4-ethyl-1-methyl-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-one in 70 ml of morpholine was refluxed for 3 hrs, concentrated on the rotary evaporator and the residue partitioned between chloroform and dilute sodium hydroxide. The chloroform was dried over anhydrous sodium sulfate and concentrated on the rotary evaporator. The residue was crystallized twice from isopropyl ether containing a small amount of ethanol, m.p. 128°-148° C. Recrystallization from toluene gave 19.5 g (61%) of product, m.p. 128°-148° C.

Workup

  1. concentrationconcentrated on the rotary evaporator
  2. customthe residue partitioned between chloroform and dilute sodium hydroxide
  3. dry with materialThe chloroform was dried over anhydrous sodium sulfate
  4. concentrationconcentrated on the rotary evaporator
  5. customThe residue was crystallized twice from isopropyl ether containing a small amount of ethanol, m.p. 128°-148° C
  6. customRecrystallization from toluene

Sources & evidence

ORD record
ord-89054f1c59674f65a50d35bff9d091ac
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Reaction notes

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