Hydrochloric Acid → N-[6-[3-[3-(phenylmethoxy)-2-pyridinyl]propoxy]hexyl]benzenemethanamine

HRID 1088719Notes

Reaction equation

HRID 1088719 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][C:12]1[C:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=[CH:14][N:13]=1.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>O>[C:20]1([CH2:19][O:18][C:17]2[C:12]([CH2:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:33][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 10340Sodium CarbonateHCID 22161756HCID 22161756, compound

Product 1

HCID 54019079N-[6-[3-[3-(phenylmethoxy)-2-pyridinyl]propoxy]hexyl]benzenemethanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-[3-[(6-Bromohexyl)oxy]propyl]-3-(phenylmethoxy)pyridine (1.0 g) was added to benzylamine (3 ml) at 120° under nitrogen. After stirring for 2 h, the solution was cooled and added to water (10 ml) and 2N hydrochloric acid (10 ml). The aqueous mixture was basified with sodium carbonate and then extracted with ethyl acetate (3×50 ml). The ethyl acetate was evaporated and the excess benzylamine was removed by distillation at reduced pressure to leave the title compound as a red oil (810 mg), t.l.c. (ethyl acetate/triethylamine 99:1) Rf 0.13.

Workup

  1. temperaturethe solution was cooled
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. customThe ethyl acetate was evaporated
  4. customthe excess benzylamine was removed by distillation at reduced pressure

Sources & evidence

ORD record
ord-cef2a0a156274c5a94832ce1c1fdbb8c
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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