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

HRID 2083695Notes

Reaction equation

HRID 2083695 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-d089f676aa5b4c24921363aa9d37e6c0
Source dataset
uspto-grants-1978_04
Patent number
US04086272

Reaction notes

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