Hydrochloric Acid → Benzyl 4-oxopiperidine-1-carboxylate

HRID 430619Notes

Reaction equation

HRID 430619 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:14]2(OCC[O:15]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:14](=[O:15])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15165038Phenylmethyl 1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylate

Product 1

HCID 643496Benzyl 4-oxopiperidine-1-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 8-benzyloxycarbonyl 1,4-dioxa-8-azaspiro[4,5] decane (0.037 mol, 10 g) in tetrahydrofuran (150 mL) was added a solution of hydrochloric acid 5% (20 mL) dropwise at room temperature. The solution was stirred for 18 h (TLC control) and then evaporated under vacuum to small volume (20 mL) and neutralized with a saturated sodium bicarbonate solution. The aqueous solution was extracted with ethyl acetate (3×100 mL) and the organic layers were dried over sodium sulfate and finally evaporated under vacuum to give 1-benzyloxycarbonyl piperidin-4-one which was substantially pure and which was used in the next step without any purification (92% yield). 1H-NMR (CDCl3): 1.63 (m, 4H); 3.56 (m,4H); 5.09 (s, 2H); 7.28 (s, 5H).

Workup

  1. customevaporated under vacuum to small volume (20 mL)
  2. extractionThe aqueous solution was extracted with ethyl acetate (3×100 mL)
  3. dry with materialthe organic layers were dried over sodium sulfate
  4. customfinally evaporated under vacuum

Sources & evidence

ORD record
ord-bf439982f7684991b0e5d3899a0ff9a5
Source dataset
uspto-grants-2001_11
Patent number
US06323214B1

Reaction notes

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