Diethyl Ether → HCID 86733862, compound

HRID 2397911Notes

Reaction equation

HRID 2397911 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 four 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-methoxy-benzyl)-α-methyl-α-phenyl-3-piperidinemethanol.

Workup

  1. additionAfter this addition
  2. temperaturerefluxed for four 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-7bdee79e1dec4c7080bd1142407865e6
Source dataset
uspto-grants-1977_05
Patent number
US04022792

Reaction notes

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