Benzylamine → N-[6-[4-[(2-Naphthalenyl)oxy]butoxy]hexyl]benzenemethanamine

HRID 358922Notes

Reaction equation

HRID 358922 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(=O)(O)[O-].[Na+]>[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[O:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:31][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 191018312-[4-[(6-Bromohexyl)oxy]butoxy]naphthalene

Product 1

HCID 19101826N-[6-[4-[(2-Naphthalenyl)oxy]butoxy]hexyl]benzenemethanamineYield 95.6%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

2-[4-[(6-Bromohexyl)oxy]butoxy]naphthalene (2.25 g) and benzylamine (3.88 g) were stirred under nitrogen at ca. 125° for 2 h. The solution was diluted with 8% sodium bicarbonate (100 ml) and extracted with diethyl ether (2×100 ml), dried and evaporated in vacuo to give an oil. Purification by FCC eluting with System C (98:2:1) gave the title compound as a yellow oil (2.3 g), t.l.c. (System C 40:10:1) Rf 0.71.

Workup

  1. extractionextracted with diethyl ether (2×100 ml)
  2. customdried
  3. customevaporated in vacuo
  4. customto give an oil
  5. customPurification by FCC
  6. washeluting with System C (98:2:1)

Sources & evidence

ORD record
ord-8fc11ce2d86c4022bc4cdae2c801e075
Source dataset
uspto-grants-1991_03
Patent number
US04997986

Reaction notes

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