Phenol → 1-Benzhydryl-3-phenoxyazetidine

HRID 1589519Notes

Reaction equation

HRID 1589519 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-bfc83dedd0984ad6a81d6ef93b1f2a5d
Source dataset
uspto-grants-1986_02
Patent number
US04571393

Reaction notes

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