N-(4-(2-Chloroethoxy)phenyl)acetamide → HCID 53636350, compound

HRID 1283975Notes

Reaction equation

HRID 1283975 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][NH:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33]([NH:36][C:37]1[CH:46]=[CH:45][C:40]([O:41][CH2:42][CH2:43]Cl)=[CH:39][CH:38]=1)(=[O:35])[CH3:34]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][N:25]([CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:43][CH2:42][O:41][C:40]2[CH:45]=[CH:46][C:37]([NH:36][C:33](=[O:35])[CH3:34])=[CH:38][CH:39]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3015848N-(4-(2-Chloroethoxy)phenyl)acetamideHCID 19838166HCID 19838166, compound

Product 1

HCID 53636350HCID 53636350, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of N-2-(3,4-dibenzyloxyphenyl)ethyl benzylamine (12.0 g.), 2-(4-acetamidophenoxy)ethyl chloride (3.1 g.) and dry dimethylformamide (10 ml.) was boiled under reflux for 10 hours. The solution was cooled, more dimethylformamide (15 ml.) added, and the precipitated solid removed by filtration. The filtrate was evaporated in vacuo to dryness and the resultant solid stirred in chloroform, after which undissolved material was removed by filtration and the filtrate was evaporated in vacuo to dryness to give the crude product, N-[2-(3,4-dibenzyloxyphenyl)ethyl]-N-[2-(4-acetamidophenoxy) ethyl]benzylamine.

Workup

  1. temperatureunder reflux for 10 hours
  2. temperatureThe solution was cooled
  3. customthe precipitated solid removed by filtration
  4. customThe filtrate was evaporated in vacuo to dryness
  5. customafter which undissolved material was removed by filtration
  6. customthe filtrate was evaporated in vacuo to dryness

Sources & evidence

ORD record
ord-4a0e921a68284b96887c8ceac643eadc
Source dataset
uspto-grants-1976_08
Patent number
US03976783

Reaction notes

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