N-Methylpiperidine → 6(Triphenylmethylamino)-2,2-dimethyl-3-(5-tetrazolyl)penam

HRID 1730317Notes

Reaction equation

HRID 1730317 reaction equation
Cl.CN1CCCCC1.[C:9]1([C:15]([NH:28][CH:29]2[C:39](=[O:40])[N:31]3[CH:32]([C:37]#[N:38])[C:33]([CH3:36])([CH3:35])[S:34][C@H:30]23)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N-:41]=[N+:42]=[N-:43].[Na+].CN1CCCCC1>C(Cl)(Cl)Cl.O.C(O)C>[C:9]1([C:15]([NH:28][CH:29]2[C:39](=[O:40])[N:31]3[CH:32]([C:37]4[NH:43][N:42]=[N:41][N:38]=4)[C:33]([CH3:36])([CH3:35])[S:34][C@H:30]23)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 12291N-MethylpiperidineHCID 33557Sodium AzideHCID 205378Piperidine, 1-methyl-, hydrochlorideHCID 70604455HCID 70604455, compound

Product 1

HCID 1784319216(Triphenylmethylamino)-2,2-dimethyl-3-(5-tetrazolyl)penam

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
53 °C

Procedure

A mixture of dry N-methylpiperidine hydrochloride (8.14 g., 0.06 mole) anhydrous ethanol free chloroform (180 ml.), 6-triphenylmethylamino-2,2-dimethyl-3-cyanopenam (13.2g, 0.03 mole), finely powdered sodium azide (3.9 g., 0.06 mole) and N-methylpiperidine (8.9 g., 0.09 mole) is heated to 53° C. (internal temperature) for 80 minutes. It is then cooled to room temperature and diluted with ethanolfree chloroform (750 ml.) and water (800 ml.). It is thoroughly shaken, thechloroform phase separated and washed successively with 1.5N HCl (1 ×1000 ml.) and water (1 × 800 ml.). The chloroform solution is filtered through anhydrous sodium sulfate and then concentrated under reduced pressure to about 300 ml. White crystals separate. The concentrateis diluted with hexane (350 ml.) and filtered after 15 minutes. The crystalline product is washed with hexane and dried in air for 15 minutes followed by drying under vacuum at 56° C. for 1 hour. Yield = 7.66 g. (52.9%).

Workup

  1. temperatureIt is then cooled to room temperature
  2. customthechloroform phase separated
  3. washwashed successively with 1.5N HCl (1 ×1000 ml.) and water (1 × 800 ml.)
  4. filtrationThe chloroform solution is filtered through anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure to about 300 ml
  6. customWhite crystals separate
  7. additionThe concentrateis diluted with hexane (350 ml.)
  8. filtrationfiltered after 15 minutes
  9. washThe crystalline product is washed with hexane
  10. customdried in air for 15 minutes
  11. customby drying under vacuum at 56° C. for 1 hour

Sources & evidence

ORD record
ord-0d5ed75f4b8d4f91899b1b27dabddf88
Source dataset
uspto-grants-1976_11
Patent number
US03992394

Reaction notes

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