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

HRID 1390928Notes

Reaction equation

HRID 1390928 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 NHR3R3, 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-4bca3849059b4b0a8f3c5d4e1f8015c6
Source dataset
uspto-grants-1979_02
Patent number
US04140779

Reaction notes

Loading…