Tetrahydrofuran → 1-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-4-piperidinol

HRID 2166620Notes

Reaction equation

HRID 2166620 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.[CH2:17]([N:24]1[CH2:29][CH2:28][C:27](=[O:30])[CH:26]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([CH3:45])([CH3:44])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:33][C:32]=2[O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].[NH4+]>CCOCC>[CH2:17]([N:24]1[CH2:29][CH2:28][C:27]([CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([OH:30])[CH:26]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([CH3:44])([CH3:45])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:33][C:32]=2[O:46][CH2:47][C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 204997831-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidoneHCID 178418471HCID 178418471, compound

Product 1

HCID 204997841-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-4-piperidinol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 0° C. solution of 7.0 mmols. of 3-phenylpropylmagnesium bromide in 7 ml. of tetrahydrofuran is slowly added a solution of 2.48 g. (5.0 mmols) of 1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidone in 10 ml. of tetrahydrofuran. The resultant mixture is stirred for one hour and is then added to 250 ml. of saturated ammonium chloride-250 ml. ether. The ether phase is dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 200 g. of silica gel eluted with 50% ether-cyclohexane to yield the title compound.

Workup

  1. customTo a 0° C.
  2. additionis then added to 250 ml
  3. dry with materialThe ether phase is dried over magnesium sulfate
  4. customevaporated
  5. customThe residue is purified via column chromatography on 200 g
  6. washof silica gel eluted with 50% ether-cyclohexane

Sources & evidence

ORD record
ord-c861c8f88e484a16b96e023683132feb
Source dataset
uspto-grants-1983_06
Patent number
US04387229

Reaction notes

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