Pyrrolidine → 1-(Naphthalen-1-yloxy)-3-pyrrolidin-1-yl-propan-2-ol

HRID 426624Notes

Reaction equation

HRID 426624 reaction equation
[O:1]1[CH:3]([CH2:4][O:5][C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][CH:7]=2)[CH2:2]1.[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1>CO>[N:16]1([CH2:2][CH:3]([OH:1])[CH2:4][O:5][C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][CH:7]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 915212-((1-Naphthalenyloxy)methyl)oxirane

Product 1

HCID 4173521-(Naphthalen-1-yloxy)-3-pyrrolidin-1-yl-propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,2-epoxy-3-(1-naphthyloxy)propane (62.0 g) and the amine of formula NHR2R3, pyrrolidine (23.5 g), in methanol (250 ml) is heated at reflux for two hours. The reaction mixture is concentrated to dryness. The oily residue is crystallized from chloroform and diethyl ether by the addition of hexane to give the title compound, mp 68°-70° C.

Workup

  1. temperatureat reflux for two hours
  2. concentrationThe reaction mixture is concentrated to dryness
  3. customThe oily residue is crystallized from chloroform and diethyl ether by the addition of hexane

Sources & evidence

ORD record
ord-ed39ba9d28dc468196b7999e17f08c7f
Source dataset
uspto-grants-1979_10
Patent number
US04170653

Reaction notes

Loading…