Hydrochloric Acid → HCID 22959133, compound

HRID 2303391Notes

Reaction equation

HRID 2303391 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.O=S(Cl)Cl.Cl>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH:13]=[C:14]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 22959135HCID 22959135, compound

Product 1

HCID 22959133HCID 22959133, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 40.0 g (123 mmol) of 4-benzyl-4-hydroxy-piperidine-1-carboxylic acid benzyl ester in 250 ml CH2Cl2 were added 39.6 ml (492 mmol) pyridine and at 0° C. 17.8 ml (246 mmol) of SOCl2. The reaction mixture was stirred for 30 min. at 0° C. and then 250 ml of aqueous (2N) HCl were added. The aqueous phase was extracted twice with CH2Cl2 and the combined organic layers were washed with water, dried over MgSO4 and the solvent was removed under reduced pressure to give 36.3 g (118 mmol, 96%) of 4-benzyl-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester as an orange oil.

Workup

  1. customat 0° C
  2. extractionThe aqueous phase was extracted twice with CH2Cl2
  3. washthe combined organic layers were washed with water
  4. dry with materialdried over MgSO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d97a1f9f4c1448448d0f8c913f8534bb
Source dataset
uspto-grants-2002_08
Patent number
US06432985B1

Reaction notes

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