Benzene → HCID 178501908, compound

HRID 1277632Notes

Reaction equation

HRID 1277632 reaction equation
C1O[C:4]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:9][C:8]2=[O:17])([NH:5]O)[O:3]C1.C1C=CC=CC=1.C(OCC)(=O)C.[K+].[Br-]>Cl.CO.C1C=CC=CC=1.C(OCC)(=O)C.C(O)=O.C(O)=O>[OH:3][C:4]1[C:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:9][C:8]=2[O:17][N:5]=1

Participants

9

Reactant 4

HCID 241BenzeneHCID 8857Ethyl AcetateHCID 253877Potassium BromideHCID 566239341-Methoxycarbonyl-3-oxopiperidine-4-carbohydroxamic acid ethylene acetal

Product 1

HCID 178501908HCID 178501908, compound

Reagents, catalysts & solvents 4

HCID 284Formic AcidSolventHCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 86737855Benzene ethyl acetate formic acidSolvent

Procedure

A solution of 1-methoxycarbonyl-3-oxopiperidine-4-carbohydroxamic acid ethylene acetal (750 mg; 2.9 mmol) in concentrated hydrochloric acid (13 ml) was heated to 70° C. for 10 minutes. The mixture was evaporated in vacuo to give a black oil. CC [silica gel (Woelm 0.063-0.1 mm): 60 g; eluents: benzene to which ethyl acetate (40-70%) and formic acid (1%) was added] gave crystalline and TLC-pure Va (244 mg; 43%) [RF : 0.27; eluent: benzene-ethyl acetate-formic acid (50:50:1)]. An analytical sample was recrystallized (benzene-cyclohexane) to give pure Va as colourless crystals, m.p. 136.0-138.0° C. IR (KBr): 3700-3300 (m), 3300-2500 (several bands, w-m), 1655 (s), 1525 (m), 1490 (s) cm-1. UV [methanol (log ε)]: 212 (3.64) nm. 1H NMR (CDCl3): δ10.6 (1H, (s), 4.43 (2H, s), 3.70 (s) and 3.8-3.5 (t) (a total of 5H), 2.6-2.3 (2H, t).

Workup

  1. customThe mixture was evaporated in vacuo
  2. customto give a black oil
  3. customgave crystalline
  4. customAn analytical sample was recrystallized (benzene-cyclohexane)
  5. customto give pure Va as colourless crystals, m.p. 136.0-138.0° C

Sources & evidence

ORD record
ord-a079bad4af484e3ba704ac76a6ef3ecf
Source dataset
uspto-grants-1981_07
Patent number
US04278676

Reaction notes

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