Methylamine → HCID 18176647, compound

HRID 394485Notes

Reaction equation

HRID 394485 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1.[CH3:15][NH2:16].[O-2].[Ca+2]>C1COCC1>[Cl:14][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[Cl:13])[O:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:16][CH3:15]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 6850728CalciumoxideHCID 187686344-(4-Bromobutoxy)-1,2-dichlorobenzene

Product 1

HCID 18176647HCID 18176647, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 4-(4-bromobutoxy)- 1,2-dichlorobenzene (0.03 mol), methylamine (20 g) and calciumoxide (7 g) in THF (100 ml) was stirred at 125° C. overnight in an autoclave. The mixture was filtered over dicalite and the filtrate was evaporated. The residue was taken up in DIPE and the mixture was filtered over dicalite. The filtrate was converted into the hydrochloric acid salt (1:1) with HCl/2-propanol. The precipitate was filtered off and dried, yielding 6 g (70.3%) of 4-(3,4-dichlorophenoxy)-N-methyl-1-butanamine (intermediate 4, mp. 132° C.).

Workup

  1. filtrationThe mixture was filtered over dicalite
  2. customthe filtrate was evaporated
  3. filtrationthe mixture was filtered over dicalite
  4. filtrationThe precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-7d09998466384c6996cf8fb9602ffc90
Source dataset
uspto-grants-2003_08
Patent number
US06602873B2

Reaction notes

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