Hydrochloric Acid → ethyl N-(2,4,6-trimethylphenylacetyl)-piperidine-2-carboxylate

HRID 847471

Reaction equation

HRID 847471 reaction equation
[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH2:9][C:10](Cl)=[O:11].[NH:14]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:15]1[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(N(CC)CC)C.Cl>O1CCCC1>[CH3:13][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH2:9][C:10]([N:14]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:15]1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27517Ethyl piperidine-2-carboxylateHCID 110307542,4,6-Trimethylbenzeneacetyl chloride

Product 1

HCID 14883010ethyl N-(2,4,6-trimethylphenylacetyl)-piperidine-2-carboxylateYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

223 g (1.125 mol) of mesityleneacetyl chloride are added dropwise at 0° to 10° C. to 182 ml (1.157 mol) of ethyl pipecolinate and 162 ml (1.157 mol) of triethylamine in 1,200 ml of absolute tetrahydrofuran (THF), followed by stirring for 1 hour at room temperature. After the mixture has been stirred into 5 liters of ice water and 500 ml of 1N HCl, the product is filtered off with suction, washed with water and dried in vacuo at 50° C. over P2O5. 342.3 g (95.2% of theory) of ethyl N-(2,4,6-trimethylphenylacetyl)-piperidine-2-carboxylate are obtained.

Workup

  1. filtrationthe product is filtered off with suction
  2. washwashed with water
  3. dry with materialdried in vacuo at 50° C. over P2O5

Sources & evidence

ORD record
ord-4932abf7be2c44e1918285ce7b6ba0e1
Source dataset
uspto-grants-1992_08
Patent number
US05142065

Linked notes

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