Isoamylamine → HCID 10108017, compound

HRID 1793480Notes

Reaction equation

HRID 1793480 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH2:12])[CH2:8][CH:9]([CH3:11])[CH3:10].[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[O:23][CH2:24][CH2:25][CH2:26][CH2:27]Cl>CS(C)=O.O>[CH2:7]([NH:12][CH2:27][CH2:26][CH2:25][CH2:24][O:23][C:14]1[CH:15]=[CH:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=1)[CH2:8][CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 7894IsoamylamineHCID 11430Potassium CarbonateHCID 116587114-(2-Naphthyloxy)-1-chlorobutane

Product 1

HCID 10108017HCID 10108017, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of anhydrous potassium carbonate (10 gm, in excess) and isoamylamine (0.21 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 140° C. for 7 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-(isoamyl)-(4-(naphthalen-2-yloxy)-butyl)amine, solid, m.p. 102° C., (yield 0.54 gm, 89.3%).

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-d1a55cd73fce4f19a47d33a5d5d31392
Source dataset
uspto-grants-2006_07
Patent number
US07081465B2

Reaction notes

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