Isopropylamine → 1-Benzyloxy-4-[3-(1-methylethyl)aminopropoxy]benzene

HRID 2417983Notes

Reaction equation

HRID 2417983 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18]Br)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20]([NH2:23])([CH3:22])[CH3:21]>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][NH:23][CH:20]([CH3:22])[CH3:21])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 111100311-(Benzyloxy)-4-(3-bromopropoxy)benzene

Product 1

HCID 133384801-Benzyloxy-4-[3-(1-methylethyl)aminopropoxy]benzene

Procedure

In a glass lined vessel, 1-benzyloxy-4-(3-bromopropoxy)benzene (33.4 g) in 300 ml of isopropylamine was heated at 100° for 10 hours under nitrogen at 1000 psi, then the excess isopropylamine was removed in vacuo and the residue was dissolved in 300 ml of water. The solution was made alkaline with 10% sodium hydroxide and the resulting oil extracted with dichloromethane. The dichloromethane extract, dried over potassium carbonate, was concentrated and distilled to yield 22.5 g of 1-benzyloxy-4-[3-(1-methylethyl)aminopropoxy]benzene, boiling range 180°-190° (0.5 mm) (97.8% pure by gas chromatography).

Workup

  1. customthe excess isopropylamine was removed in vacuo
  2. dissolutionthe residue was dissolved in 300 ml of water
  3. extractionthe resulting oil extracted with dichloromethane
  4. extractionThe dichloromethane extract
  5. dry with materialdried over potassium carbonate
  6. concentrationwas concentrated
  7. distillationdistilled

Sources & evidence

ORD record
ord-df6fbda604b34d58a22b9567905b59b2
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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