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Water → HCID 12874828, compound

HRID 848516
Notes
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Reaction equation

HRID 848516 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:16])[CH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[OH:8].Cl[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.O>CN(C)C=O>[CH3:16][N:4]([CH3:3])[CH2:5][CH2:6][CH:7]([O:8][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 74741-Chloro-4-nitrobenzeneHCID 24758Sodium hydrideHCID 4264951-(4-Chlorophenyl)-3-(dimethylamino)propan-1-ol

Product 1

HCID 12874828HCID 12874828, compoundYield 116.1%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

2.85 g of sodium hydride in a 50% oil suspension were added at 20° C. to a solution of 6.32 g of α-[2-dimethylamino-ethyl]-4-chlorobenzene methanol in 60 ml of dimethylformamide and 5.1 g of p-chloronitrobenzene were added thereto under nitrogen. The mixture was stirred for 45 minutes and 100 ml of water were added thereto at 25° C. The mixture was extracted with methylene chloride and the organic phase was washed with water, dried and evaporated to dryness to obtain 11.5 g of N,N-dimethyl-γ-(4-nitrophenoxy)-4-chlorobenzene-propanamine in the form of an orange oil.

Workup

  1. additionwere added
  2. customat 25° C
  3. extractionThe mixture was extracted with methylene chloride
  4. washthe organic phase was washed with water
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-3debfbd8915140e4a3a37d459638d0de
Source dataset
uspto-grants-1981_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04296126

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes