Acetic Acid → HCID 12909687, compound

HRID 2107371Notes

Reaction equation

HRID 2107371 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][CH:5]([NH:14][CH3:15])[C:6]1[CH:11]=[CH:10]C(OC)=C[CH:7]=1.[C:20]([O:28][CH2:29][CH3:30])(OCC)(OCC)C.[C:31](O)(=O)[CH3:32]>>[CH3:31][C:32]1[N:14]([CH3:15])[CH:5]([C:6]2[CH:7]=[CH:30][C:29]([O:28][CH3:20])=[CH:10][CH:11]=2)[CH2:4][C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=2[N:1]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 66221Triethyl orthoacetateHCID 12909670HCID 12909670, compound

Product 1

HCID 12909687HCID 12909687, compound

Conditions

Temperature
112 °C

Procedure

A stirred solution of 4.10 g of 2-amino-α-(4-methoxyphenyl)-N-methylphenethylamine, 16.22 g of triethyl orthoacetate and 5.6 ml of glacial acetic acid is held under reflux (bath temperature 112° C.) for 2 hours. AFter standing overnight at ambient temperature the solution is concentrated in vacuo (pump) at 90° C. on a rotary evaporator. An ethereal solution of the residual oil is washed with 5% hydrochloric acid. The aqueous phase is made alkaline with 50% sodium hydroxide solution and the mixture is extracted twice with 25 ml-portions of methylene chloride. The combined, (dried over anhydrous sodium sulfate) organic phase is evaporated to afford a solid. Recrystallization from 10 ml of acetonitrile provides tan crystals, mp 130°-132° C. of 4,5-dihydro-2,3-dimethyl-4-(4-methoxyphenyl)-3H-1,3-benzodiazepine.

Workup

  1. concentrationthe solution is concentrated in vacuo (pump) at 90° C. on a rotary evaporator
  2. washAn ethereal solution of the residual oil is washed with 5% hydrochloric acid
  3. extractionthe mixture is extracted twice with 25 ml-portions of methylene chloride
  4. dry with material(dried over anhydrous sodium sulfate) organic phase
  5. customis evaporated
  6. customto afford a solid
  7. customRecrystallization from 10 ml of acetonitrile

Sources & evidence

ORD record
ord-34548c4613694c6cbbc9314ff541fe97
Source dataset
uspto-grants-1990_06
Patent number
US04933493

Reaction notes

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