Triethylamine → HCID 68139297, compound

HRID 1288162Notes

Reaction equation

HRID 1288162 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16][C:6]3=[C:5]([CH3:17])[C:4]=2[CH:3]=1.C(N(CC)CC)C.[Cl:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].[OH-].[Na+]>C1C=CC=CC=1>[ClH:25].[CH2:29]([O:28][C:26]([N:14]1[CH2:15][CH2:16][C:6]2[C:7](=[N:8][C:9]3[CH:10]=[CH:11][C:2]([CH3:1])=[CH:3][C:4]=3[C:5]=2[CH3:17])[CH2:12][CH2:13]1)=[O:27])[CH3:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 21503586HCID 21503586, compound

Product 1

HCID 68139297HCID 68139297, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

1.1 gm (5 millimols) of 9,11-dimethyl-1,2,4,5-tetrahydro-3H-azepino[4,5-b]quinoline were dissolved in 30 ml of benzene, and a solution of 1 gm (10 millimols) of triethylamine in 10 ml of benzene and then 1.08 gm (10 millimols) of ethyl chloroformate were added, and the resulting mixture was heated at its boiling point for 2 hours. The cooled reaction mixture was admixed with 50 ml of ice water, and the aqueous mixture was made alkaline with 2 N sodium hydroxide. The benzene phase was separated, and the aqueous layer was extracted with chloroform. The benzene phase and the chloroform extract were combined, dried over sodium sulfate, and the solvents were distilled off. For conversion into the hydrochloride, the residual base was dissolved in hot acetone, and the solution was acidified with isopropanolic hydrochloric acid, whereupon the hydrochloride crystallized out.

Workup

  1. temperaturethe resulting mixture was heated at its boiling point for 2 hours
  2. customThe cooled reaction mixture
  3. customThe benzene phase was separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. extractionThe benzene phase and the chloroform extract
  6. dry with materialdried over sodium sulfate
  7. distillationthe solvents were distilled off
  8. dissolutionFor conversion into the hydrochloride, the residual base was dissolved in hot acetone
  9. customcrystallized out

Sources & evidence

ORD record
ord-e567144aee8a4a91bb4ff6163df8095a
Source dataset
uspto-grants-1976_10
Patent number
US03987047

Reaction notes

Loading…