Water → trans-3-[3-(Dimethylamino)propyl]-1,2,3,4-tetrahydro-2-naphthalenol

HRID 263229Notes

Reaction equation

HRID 263229 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][Li])[CH3:3].[O:8]1[CH:18]2[CH:9]1[CH2:10][C:11]1[C:16]([CH2:17]2)=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CCOCC>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][C@@H:18]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]1[OH:8]

Participants

5

Reactant 3

HCID 962WaterHCID 108880512,3-Epoxy-1,2,3,4-tetrahydronaphthaleneHCID 178506872HCID 178506872, compound

Product 1

HCID 70608078trans-3-[3-(Dimethylamino)propyl]-1,2,3,4-tetrahydro-2-naphthalenol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

to a solution of 0.1 mol of dimethylamino propyllithium in 500 ml of ether cooled to 0°-5° C. is added dropwise a solution of 7.3 g (0.05 mol) of 2,3-epoxy-1,2,3,4-tetrahydronaphthalene in 100 ml of ether. The reaction mixture is then heated under reflux for 2 hours and decomposed with water. The organic layer is separated and dried and the desired 1,2,3,4-tetrahydro-3-(3-dimethylaminopropyl)-2-naphthalenol separated from byproducts by column chromatography on neutral alumina.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureunder reflux for 2 hours
  3. customThe organic layer is separated
  4. customdried
  5. customthe desired 1,2,3,4-tetrahydro-3-(3-dimethylaminopropyl)-2-naphthalenol separated from byproducts by column chromatography on neutral alumina

Sources & evidence

ORD record
ord-13dfe2b2b8604b15bc1710fe4af5a99c
Source dataset
uspto-grants-1979_05
Patent number
US04156723

Reaction notes

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