(3-Phenoxypropyl)amine → HCID 18793109, compound

HRID 1004661Notes

Reaction equation

HRID 1004661 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1>CC(O)C>[BrH:12].[O:1]([CH2:8][CH2:9][CH2:10][NH:11][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 418237(3-Phenoxypropyl)amineHCID 128339324-(2-Bromoethoxy)phenol

Product 1

HCID 18793109HCID 18793109, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of 3-phenoxy-1-propanamine (24.2 g, 160 mmol) in 100 mL of 2-propanol is heated to reflux and treated slowly with a solution of 4-(2-bromoethoxy)phenol (17.4 g, 80 mmol) in 150 mL of 2-propanol. The mixture is heated at reflux for 4 days, then cooled and partitioned between ethyl ether and aqueous sodium bicarbonate solution. The organic layer is evaporated and the residue recrystallized from ethanol to give 6.0 g (20%) of product, mp 204-205° C.

Workup

  1. temperatureto reflux
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 4 days
  4. temperaturecooled
  5. custompartitioned between ethyl ether and aqueous sodium bicarbonate solution
  6. customThe organic layer is evaporated
  7. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-50cbc68476f0437fab867d4923e6dbc5
Source dataset
uspto-grants-2000_04
Patent number
US06051605

Reaction notes

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