Diethyl Ether → HCID 21559974, compound

HRID 1578402Notes

Reaction equation

HRID 1578402 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.C([Li])CCC.[CH2:17]([N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C:25]1=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC[O:33]CC>>[CH2:17]([N:24]1[CH2:29][CH2:28][C:27]([OH:33])([C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=2)[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 51700761-Benzyl-2-piperidoneHCID 178418339Butyllithium

Product 1

HCID 21559974HCID 21559974, compound

Procedure

A solution of 22.5 g. (0.1 mol) of p-bromobenzotrifluoride in 50 ml. of ether is stirred under argon at ice-bath temperature while 50 ml. of 2M butyl lithium solution is added dropwise. The solution is then stirred at room temperature for 15 minutes, and then cooled again to 0°C. A solution of 17.7 g. of N-benzylpiperidone in 50 ml. of ether is then added over 30 minutes and the reaction is stirred at room temperature for 3 hours. The solution is poured into cracked ice-water and filtered to remove some solid. The filtrate is diluted with methylene chloride, and the organic layer is dried and evaporated. The residue is triturated with petroleum ether (b.p. 30°-60°C.), and the solid is collected, washed with ether and dried to give white solid, m.p. 115°-117°C.

Workup

  1. temperaturecooled again to 0°C
  2. stirringthe reaction is stirred at room temperature for 3 hours
  3. filtrationfiltered
  4. customto remove some solid
  5. additionThe filtrate is diluted with methylene chloride
  6. customthe organic layer is dried
  7. customevaporated
  8. customThe residue is triturated with petroleum ether (b.p. 30°-60°C.)
  9. customthe solid is collected
  10. washwashed with ether
  11. customdried
  12. customto give white solid, m.p. 115°-117°C.

Sources & evidence

ORD record
ord-40835fa2fe5f41df8c6ac0ddd9fd873c
Source dataset
uspto-grants-1976_02
Patent number
US03936464

Reaction notes

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