Hydrochloric Acid → N-[5-[3-(4-Methoxyphenyl)propoxy]pentyl]benzenemethanamine hydrochloride

HRID 2166160Notes

Reaction equation

HRID 2166160 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[ClH:27]>O>[ClH:27].[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 197980251-[3-[(5-Bromopentyl)oxy]propyl]-4-methoxybenzene

Product 1

HCID 20062857N-[5-[3-(4-Methoxyphenyl)propoxy]pentyl]benzenemethanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-[3-[(5-Bromopentyl)oxy]propyl]-4-methoxybenzene (2.0 g) was added to benzylamine (6 ml) at 120° under nitrogen. The solution was stirred for 2 h at 120° then added (hot) to 2N hydrochloric acid (50 ml) and water (25 ml). The resulting precipitate was collected by filtration, washed with 2N hydrochloric acid, water and ER then dried at 50° under vacuum to give the title compound as a white solid (1.79 g) m.p. 118°-121°. The following compound was prepared in a similar manner:

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with 2N hydrochloric acid, water and ER
  3. customthen dried at 50° under vacuum

Sources & evidence

ORD record
ord-2c9325fea5a64b7eaecc18b92831e77b
Source dataset
uspto-grants-1990_07
Patent number
US04943591

Reaction notes

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