Ammonium Chloride → alpha-(2-Phenylethyl)-4-piperidinemethanol

HRID 380502Notes

Reaction equation

HRID 380502 reaction equation
I[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([Li])(C)(C)C.C(OC([N:22]1[CH2:27][CH2:26][CH:25]([CH:28]=[O:29])[CH2:24][CH2:23]1)=O)(C)(C)C.[NH4+].[Cl-]>CCOCC>[C:4]1([CH2:3][CH2:2][CH:28]([CH:25]2[CH2:26][CH2:27][NH:22][CH2:23][CH2:24]2)[OH:29])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 28503Benzene, (2-iodoethyl)-HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 178418306HCID 178418306, compound

Product 1

HCID 18364839alpha-(2-Phenylethyl)-4-piperidinemethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a solution of 5 mL (34.5 mmol) of (2-iodoethyl)benzene in 100 mL of ether at −78° C. was added 42.6 mL (72.5 mmol) of t-butyl lithium. The reaction mixture was warmed to −20° C. for 20 min, then cooled to −78° C. TO this solution, was added a solution of 5.6 g (23.2 mmol) of 1-t-butoxy carbonyl-4-formylpiperidine in 50 mL of ether and the reaction mixture was stirred 15 min at −78° C. To the reaction mixture was added 150 mL of a sat'd solution of NH4Cl and the mixture was extracted with ethyl acetate. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. Removal of the BOC protecting group was achieved as described in Example 233, Step 6 to give the title compound.

Workup

  1. temperaturecooled to −78° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic fractions were washed with sat'd NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customRemoval of the BOC protecting group

Sources & evidence

ORD record
ord-1336cf9f4f1f425ab847914893b555a9
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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