Benzylamine → HCID 23045075, compound

HRID 2108029Notes

Reaction equation

HRID 2108029 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][N:11]=1.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][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]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 23045065HCID 23045065, compound

Product 1

HCID 23045075HCID 23045075, compound

Procedure

From 2-[2-[(5-bromopentyl)oxy]ethyl]pyridine (6.04 g) and benzylamine (33 ml). After 1 h at 130° the reaction mixture was cooled and partitioned between ethyl acetate (400 ml) and 8% aqueous sodium bicarbonate (250 ml). The final product was purified by FCC eluting with ethyl acetate-triethylamine (100:1) to give the title compound as a pale yellow oil (4.18 g), t.l.c. (ethyl acetate+few drops triethylamine) Rf 0.14.

Workup

  1. temperatureAfter 1 h at 130° the reaction mixture was cooled
  2. custompartitioned between ethyl acetate (400 ml) and 8% aqueous sodium bicarbonate (250 ml)
  3. customThe final product was purified by FCC
  4. washeluting with ethyl acetate-triethylamine (100:1)

Sources & evidence

ORD record
ord-6d20cf64dfae44bea846033229580f1b
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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