Benzene → HCID 20269179, compound

HRID 485833Notes

Reaction equation

HRID 485833 reaction equation
N[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][N:9]([CH3:12])[CH2:8][CH:7]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C=CC=CC=1.Cl[C:26]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27].[OH-].[NH4+:34]>O>[CH2:29]([O:28][C:26]([C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]([NH2:34])[N:9]([CH3:12])[CH2:8][CH:7]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:27])[CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 241Benzene2×HCID 4528NomifensineHCID 14923Ammonium HydroxideHCID 61140Butyl chloroformate

Product 1

HCID 20269179HCID 20269179, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.4 g (0.01 mole) of 8-amino-4-phenyl-2-methyl-1,2,3,4-tetrahydro-isoquinoline and 100 ml of anhydrous benzene is admixed with a solution of 1.4 g (0.012 mole) of butyl chloroformate and 10 ml of anhydrous benzene and the reaction mixture is heated to boiling for 2 hours. After cooling the mixture is diluted with 50 ml of icecold water, the pH is adjusted to 9 by adding a concentrated ammonium hydroxide solution, the benzene phase is separated and extracted twice with 20 ml of benzene each, dried over anhydrous sodium sulfate and evaporated in vacuo. Thus 3.6 g of an orange oil are obtained. The product is recrystallized twice from ethanol to give 1.8 g of the title compound, yield 52.9%. Mp: 106° C. (white powder)

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureAfter cooling the mixture
  3. customthe benzene phase is separated
  4. extractionextracted twice with 20 ml of benzene each,
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-38b9a571a694434eac66e6b2ca95e580
Source dataset
uspto-grants-1985_08
Patent number
US04537895

Reaction notes

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