Benzylamine → HCID 23045269, compound

HRID 2108136Notes

Reaction equation

HRID 2108136 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:27][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 23045258HCID 23045258, compound

Product 1

HCID 23045269HCID 23045269, compoundYield 82.5%

Procedure

A solution of 2-[2-[2-[(6-bromohexyl)oxy]ethoxy]ethyl]pyridine (1.55 g) in benzylamine (3.1 g) was heated at 125° under nitrogen for 3 h. The solution was allowed to cool and then partitioned between 8% sodium bicarbonate (100 ml) and diethyl ether (2×100 ml). The solvent was evaporated in vacuo and the residual oil distilled (Kugelrohr) to remove excess benzylamine. Purification by FCC eluting with System G 92:8:1) gave the title compound (1.38 g) as a colourless oil. T.l.c. (System G 95:5:1) Rf 0.14

Workup

  1. temperatureto cool
  2. custompartitioned between 8% sodium bicarbonate (100 ml) and diethyl ether (2×100 ml)
  3. customThe solvent was evaporated in vacuo
  4. distillationthe residual oil distilled (Kugelrohr)
  5. customto remove excess benzylamine
  6. customPurification by FCC
  7. washeluting with System G 92:8:1)

Sources & evidence

ORD record
ord-bb59f4573daa4b81b2e6d49315906624
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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