Phenol → 1-Benzhydryl-3-phenoxyazetidine

HRID 2164527Notes

Reaction equation

HRID 2164527 reaction equation
[NH2-].[Na+].C1(C)C=CC=CC=1.[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:17]1([CH:23]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:24]2[CH2:27][CH:26](OS(C)(=O)=O)[CH2:25]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[C:17]1([CH:23]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:24]2[CH2:27][CH:26]([O:16][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:25]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 1140Toluene3×HCID 24533Sodium amideHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 28175781-Benzhydryl-3-phenoxyazetidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred suspension of 8.6 g. (0.22 mole) of sodium amide in 100 ml. of dry toluene was added 18.2 g. (0.2 mole) of phenol in 50 ml. of dry toluene. After stirring for 2 hrs. at 60° C. the pot temperature was raised to 80° C. and a solution of 1-diphenylmethyl-3-methylsulfonyloxyazetidine (63.4 g., 0.2 mole) in 200 ml. of dry toluene was added dropwise. After an additional 2 hrs. at 80° C. the cooled mixture was treated with water, the toluene layer was extracted with dilute sodium hydroxide solution, dried and concentrated at reduced pressure. The residue was crystallized twice from a water-isopropanol mixture. The free base melted at 83°-85° C.

Workup

  1. additionTo a stirred suspension of 8.6 g
  2. waitAfter an additional 2 hrs
  3. extractionthe toluene layer was extracted with dilute sodium hydroxide solution
  4. customdried
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was crystallized twice from a water-isopropanol mixture

Sources & evidence

ORD record
ord-021ad07f8cb341579ea1f7452549f669
Source dataset
uspto-grants-1985_03
Patent number
US04505907

Reaction notes

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