Benzylamine → HCID 9972381, compound

HRID 1793470Notes

Reaction equation

HRID 1793470 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[O:25][CH2:26][CH2:27][CH2:28][CH2:29]Cl>CS(C)=O.O>[CH2:7]([NH:14][CH2:29][CH2:28][CH2:27][CH2:26][O:25][C:16]1[CH:17]=[CH:18][C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 116587114-(2-Naphthyloxy)-1-chlorobutane

Product 1

HCID 9972381HCID 9972381, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of anhydrous potassium carbonate (10 gm, in excess) and benzylamine (0.34 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 4-(2-naphthyloxy)-1-chlorobutane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 150° C. for 5 hrs. and the reaction was completed as checked by TLC. Reaction mixture was poured in distilled water (60 ml) and extracted with ethyl acetate thrice. The organic layer was separated and concentrated to get oily compound which was later crystallized by benzene hexane to get N-benzyl-[4-(naphthalen-2-yloxy)-butyl]amine, solid, m.p. 105° C., (yield 0.62 gm, 95.3%).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. extractionextracted with ethyl acetate thrice
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. customto get oily compound which
  7. customwas later crystallized by benzene hexane

Sources & evidence

ORD record
ord-ede520b1da234a4faea4ad902d89bfcb
Source dataset
uspto-grants-2006_07
Patent number
US07081465B2

Reaction notes

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