Pyridine → t-Butyl 4-(4-ethoxycarbonylamino-phenyl)-piperidine-1-carboxylate

HRID 1900085Notes

Reaction equation

HRID 1900085 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23].N1C=CC=CC=1>C(Cl)Cl>[CH2:25]([O:24][C:22]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1)=[O:23])[CH3:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate

Product 1

HCID 23371871t-Butyl 4-(4-ethoxycarbonylamino-phenyl)-piperidine-1-carboxylateYield 55.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8.84 g (32.0 mmol) of t-butyl 4-(4-aminophenyl)-piperidine-1-carboxylate were dissolved in 150ml of methylene chloride and treated with 3.82 g (35.2 mmol) of ethyl chloroformate in the presence of 2.78 g (35.2 mmol) of pyridine. The reaction mixture was stirred at room temperature for 16 hours. Thereafter, it was washed with water and the organic phase was dried over sodium sulfate, filtered and evaporated. The residue (11.3 g) was chromatographed on 95 g of silica gel 60 with ether/n-hexane (4:6). After recrystallization from ether/n-hexane there were obtained 6.15 g of t-butyl 4-(4-ethoxycarbonylamino-phenyl)-piperidine-1-carboxylate. M.p.: 126°-128°.

Workup

  1. washThereafter, it was washed with water
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue (11.3 g) was chromatographed on 95 g of silica gel 60 with ether/n-hexane (4:6)
  6. customAfter recrystallization from ether/n-hexane there

Sources & evidence

ORD record
ord-f9830ce84748488ea495eb73b0c0a207
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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