Sodium Chloride → HCID 13083939, compound

HRID 1902845Notes

Reaction equation

HRID 1902845 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:36]=[CH:35][C:8]([O:9][CH2:10][CH2:11][CH2:12][N:13]2[CH:18]3[CH2:19][CH2:20][CH:14]2[CH2:15][C:16]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[O:27])([O:21][Si](C)(C)C)[CH2:17]3)=[CH:7][CH:6]=1.[Cl-].[Na+]>>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][CH2:11][CH2:12][N:13]2[CH:14]3[CH2:20][CH2:19][CH:18]2[CH2:17][C:16]([C:26]([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)=[O:27])([OH:21])[CH2:15]3)=[CH:35][CH:36]=1

Participants

4

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 57280516HCID 57280516, compound

Product 1

HCID 13083939HCID 13083939, compound

Procedure

9 ml. of an aqueous solution containing 0.70 g (0.0174 mol) of sodium hydroxide is added and the solution obtained in Step A, above, stirred for 7 hours. Sodium chloride is added to saturate the aqueous solution followed by 100 ml. of diethyl ether. The solution is agitated, the layers partitioned, and the ethereal solution is dried over anhydrous sodium sulfate. The solution is concentrated in vacuo to afford a yellow oil. After drying on a vacuum pump for 3 hours, the oily solid is recrystallized from 300 ml. of a hot mixture of hexane isomers. The resulting solid is recrystallized from 100 ml. of hot hexanes to afford the title product, {8-[3-(4-methoxyphenoxy)propyl]-3-hydroxy-8-azabicyclo-[3.2.1]oct-3-yl}-4-fluorophenyl methanone; m.p. 100°-101° C.

Workup

  1. additionis added
  2. concentrationto saturate the aqueous solution
  3. customthe layers partitioned
  4. dry with materialthe ethereal solution is dried over anhydrous sodium sulfate
  5. concentrationThe solution is concentrated in vacuo
  6. customto afford a yellow oil
  7. customAfter drying on a vacuum pump for 3 hours
  8. customthe oily solid is recrystallized from 300 ml
  9. additionof a hot mixture of hexane isomers
  10. customThe resulting solid is recrystallized from 100 ml

Sources & evidence

ORD record
ord-7b37f8be64ae4977aacb1160cf1bafe1
Source dataset
uspto-grants-1982_12
Patent number
US04366154

Reaction notes

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