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

HRID 1439714Notes

Reaction equation

HRID 1439714 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 2 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 2 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-f54abc0d470842bca4d2368d5c156b43
Source dataset
uspto-grants-1977_11
Patent number
US04060613

Reaction notes

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