Diethyl Ether → HCID 86733862, compound

HRID 1283984Notes

Reaction equation

HRID 1283984 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7]C=[CH:5][CH:4]=1.[C:9]([C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:13]1[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)(=[O:11])[CH3:10].[Cl-].[NH4+].[CH2:36](OCC)C>>[CH2:18]([N:14]1[CH2:15][CH2:16][CH2:17][C@H:12]([C:9]([CH3:36])([C:10]2[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=2)[OH:11])[C@@H:13]1[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 7961BromobenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 68126335HCID 68126335, compound

Product 1

HCID 86733862HCID 86733862, compound

Procedure

To the Grignard reagent prepared from 2.4 g. of magnesium turnings and 15.7 g. of bromobenzene in diethyl ether there is added dropwise an ethereal solution of 33.7 g. of cis-3-acetyl-1-benzyl-2-(p-methoxybenzyl)piperidine. After this addition is completed, the reaction mixture is stirred and refluxed for 4 hours and poured into aqueous ammonium chloride solution. The ether layer is separated, dried, and filtered. The filtrate is evaporated to dryness under reduced pressure to yield cis-1-benzyl-2-(p-methoxybenzyl)-α-methyl-α-phenyl-3-piperidinemethanol.

Workup

  1. additionAfter this addition
  2. temperaturerefluxed for 4 hours
  3. customThe ether layer is separated
  4. customdried
  5. filtrationfiltered
  6. customThe filtrate is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-3145f2f9af6947ccb823104cf4a48638
Source dataset
uspto-grants-1976_08
Patent number
US03976653

Reaction notes

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