Phenol → N-butyl-N-(3-phenoxypropyl)butan-1-amine

HRID 1855320

Reaction equation

HRID 1855320 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl.Cl[CH2:12][CH2:13][CH2:14][N:15]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19]>O>[CH2:20]([N:15]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:14][CH2:13][CH2:12][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 225950531-Dibutylamino-3-chloropropane hydrochloride

Product 1

HCID 5262101N-butyl-N-(3-phenoxypropyl)butan-1-amineYield 91.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The process is performed in the same manner as previously (Example 13), starting with 138 g (1.466 mol; 1.15 eq.) of phenol, 109.5 g (2.738 mol; 2.15 eq.) of NaOH, 530 ml of distilled water and 308.9 g (1.275 mol; 1 eq.) of N-(3-chloropropyl)-N,N-dibutylamine hydrochloride. The mixture is refluxed for 16 hours. The oil formed is separated out by settling and washed with 500 ml of water and then diluted with 500 ml of MTBE and washed with 500 ml of 2% HCl. The MTBE phase is concentrated under vacuum and the oil is dried by azeotropic distillation with DCM. 307.1 g of the crude derivative N,N-dibutyl-N-(3-phenoxypropyl)amine are obtained.

Workup

  1. temperatureThe mixture is refluxed for 16 hours
  2. customThe oil formed
  3. customis separated out
  4. washwashed with 500 ml of water
  5. additiondiluted with 500 ml of MTBE
  6. washwashed with 500 ml of 2% HCl
  7. concentrationThe MTBE phase is concentrated under vacuum
  8. dry with materialthe oil is dried by azeotropic distillation with DCM

Sources & evidence

ORD record
ord-cededdaf22534e1cb4d123dcd746a4ca
Source dataset
uspto-grants-2015_02
Patent number
US08962869B2

Linked notes

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