Dimethylamine → Ammonium Hydroxide

HRID 414478

Reaction equation

HRID 414478 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[O:15][CH2:16][CH2:17]Cl)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[CH3:19][NH:20][CH3:21].O>C(O)O>[OH-:15].[NH4+:20].[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[O:15][CH2:16][CH2:17][N:20]([CH3:21])[CH3:19])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 212808202-(9-Anthryloxy)ethyl chloride

Product 2

HCID 14923Ammonium HydroxideHCID 143732391-(9-Anthryloxy)-2-dimethylaminoethane

Reagents, catalysts & solvents 1

HCID 79015MethanediolSolvent

Procedure

2-(9-Anthryloxy)ethyl chloride (5.0 g) was heated for 5 hours at 90° C. in methylene glycol (50 ml) containing dimethylamine (4.0 g) using a dry ice condenser. The solution was cooled and added to water. The resulting mixture was extracted with ethyl acetate, and the extract dried and evaporated. The crude product was chromatographed on 100 g silica gel, eluting with a solution of methylene chloride:methanol:ammonium hydroxide, 95:5:1, to yield 1-(9-anthryloxy)-2-dimethylaminoethane, which was converted to the maleate, mp 132°-134° C.

Workup

  1. temperatureThe solution was cooled
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. customthe extract dried
  4. customevaporated
  5. customThe crude product was chromatographed on 100 g silica gel
  6. washeluting with a solution of methylene chloride

Sources & evidence

ORD record
ord-1e384aad5b3746e8bd63ec7d19772340
Source dataset
uspto-grants-1988_12
Patent number
US04792551

Linked notes

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