Ethyl chloroformate → HCID 70624874, compound

HRID 1112206Notes

Reaction equation

HRID 1112206 reaction equation
[C:1]1([CH:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:10][CH:9]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21][N:8]23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:22]([O:24][C:25](Cl)=[O:26])[CH3:23].[OH-].[Na+]>C(Cl)(Cl)Cl.O>[CH2:22]([O:24][C:25]([N:19]1[CH2:18][CH2:17][CH:9]2[N:8]([CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:10]2)[CH2:21][CH2:20]1)=[O:26])[CH3:23]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 70624869HCID 70624869, compound

Product 1

HCID 70624874HCID 70624874, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

5.4 g of (7RS,12aRS)-1,2,3,4,5,7,12,12a-octahydro-7-phenyl-1,4-diazepino[1,7-b]isoquinoline was dissolved in 75 cc of chloroform and 30 cc of water are added. 4.3 g of chloroformic acid ethyl ester and subsequently a solution of 1.58 g of sodium hydroxide in 30 cc of water were added dropwise at a temperature of 0°-5°. The reaction mixture was stirred for another hour without cooling. The layers were then separated and the organic phase was washed twice with water. After drying with magnesium sulphate and concentration by evaporation of the filtered chloroform solution, the (7RS,12aRS)-1,2,3,4,5,7,12,12a-octahydro-7-phenyl-1,4-diazepino[1,7-b]isoquinoline-3-carboxylic acid ethyl ester was obtained in crude form.

Workup

  1. temperaturewithout cooling
  2. customThe layers were then separated
  3. washthe organic phase was washed twice with water
  4. dry with materialAfter drying with magnesium sulphate and concentration by evaporation of the filtered chloroform solution

Sources & evidence

ORD record
ord-6e42fafb806a4a3aa476fcaccb2234f6
Source dataset
uspto-grants-1978_10
Patent number
US04120965

Reaction notes

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