2-Chloro-N,N-dimethylethylamine → HCID 21873475, compound

HRID 723355Notes

Reaction equation

HRID 723355 reaction equation
[H-].[Na+].[CH3:3][O:4][CH:5]([O:15][CH3:16])[CH2:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20]Cl>CN(C)C=O.C(OCC)(=O)C>[CH3:16][O:15][CH:5]([O:4][CH3:3])[CH2:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:20][CH2:19][N:18]([CH3:22])[CH3:17])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 21873414HCID 21873414, compound

Product 1

HCID 21873475HCID 21873475, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (1.57 g) was added to a solution of 4-(2,2-dimethoxyethyl-amino)phenol (4.3 g) in dimethylformamide (25 mL). After 30 minutes, 2-dimethylaminoethyl chloride (hydrochloride, 3.14 g) was added. After 12 hours, the reaction solution was diluted with ethyl acetate and washed with water. The organic phase was dried and concentrated. The residue was purified by MPLC (eluent: dichloromethane/methanol/ammonia solution 95:4.9:0.1). The product with the molecular weight of 268.36 (C14H24N2O3); MS (ESI): 269 ([M+H]+), was obtained in this way.

Workup

  1. waitAfter 12 hours
  2. washwashed with water
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customThe residue was purified by MPLC (eluent: dichloromethane/methanol/ammonia solution 95:4.9:0.1)
  6. customMS (ESI): 269 ([M+H]+), was obtained in this way

Sources & evidence

ORD record
ord-9b15dc935e9048bdbf41f30abf19b0ea
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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