Benzylamine → N-[5-(2-Phenylethoxy)pentyl]benzenemethanamine

HRID 1032704Notes

Reaction equation

HRID 1032704 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>Cl>[C:10]1([CH2:9][CH2:8][O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 197980262-(5-Bromopentoxy)ethylbenzene

Product 1

HCID 20062790N-[5-(2-Phenylethoxy)pentyl]benzenemethanamine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

[2-[(5-Bromopentyl)oxy]ethyl]benzene (10.0 g) was added over 1 h to benzylamine (30 ml) at ca. 120° under nitrogen. After 2 h at 120° the reaction mixture was added to 2N hydrochloric acid (200 ml), the mixture was extracted with ethyl acetate (2×250 ml) and the combined organic extracts were washed with 2N sodium carbonate, water and brine, dried and concentrated in vacuo to give the title compound as a pale yellow oil (8.6 g), t.l.c. (ethyl acetate-triethylamine 99:1) Rf 0.78

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×250 ml)
  2. washthe combined organic extracts were washed with 2N sodium carbonate, water and brine
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbe693a4e02c4c20bbc77f3a0b8eeb03
Source dataset
uspto-grants-1990_09
Patent number
US04959381

Reaction notes

Loading…