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

HRID 1730318Notes

Reaction equation

HRID 1730318 reaction equation
[C:1]1([C:7]([NH:20][CH:21]2[C:31](=[O:32])[N:23]3[CH:24]([C:29]#[N:30])[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]23)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:33]=[N+:34]=[N-:35].[Na+].CN1CCCCC1.Cl.CN1CCCCC1>C(O)C.O>[C:1]1([C:7]([NH:20][CH:21]2[C:31](=[O:32])[N:23]3[CH:24]([C:29]4[NH:35][N:34]=[N:33][N:30]=4)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]23)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 12291N-Methylpiperidine2×HCID 33557Sodium Azide2×HCID 205378Piperidine, 1-methyl-, hydrochloride2×HCID 70604455HCID 70604455, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent4×HCID 962WaterSolvent

Procedure

A mixture of 6-triphenylmethylamino-2,2-dimethyl-3-cyanopenam (4.39 g. 0.01mole), anhydrous ethanol-free chloroform (20 ml.), powdered sodium azide (650 mg., 0.01 mole) and dry N-methylpiperidine (2.98 g., 0.03 mole) is heated to 58°-60° C. (internal temperature). To the mixture is added with stirring 5 ml. of a solution of dry N-methylpiperidine hydrochloride (1.5 g., 0.011 mole) in ethanol-free chloroform (20 ml.) every 15 minutes over a period of one hour. The mixture is stirred and heated for 1.5 hours at 58°-60° C. following the additions of N-methylpiperidine and is then charged with finely powdered sodium azide (650 mg.) and N-methylpiperidine hydrochloride (1.5 g., 0.011 mole) in ethanol-free chloroform (20 ml.). The reaction mixture is heated for anadditional hour and is then cooled to room temperature and diluted with water (150 ml.) and ethanol-free chloroform (250 ml.). The mixture is thoroughly shaken and the chloroform phase then separated and washed with successively with 1N HCl (1 × 250 ml.) and water (1 × 150 ml.).

Workup

  1. temperatureis heated to 58°-60° C. (internal temperature)
  2. additionTo the mixture is added
  3. stirringThe mixture is stirred
  4. temperatureheated for 1.5 hours at 58°-60° C.
  5. temperatureThe reaction mixture is heated for anadditional hour
  6. stirringThe mixture is thoroughly shaken
  7. customthe chloroform phase then separated
  8. washwashed with successively with 1N HCl (1 × 250 ml.) and water (1 × 150 ml.)

Sources & evidence

ORD record
ord-0293fe8ab31a40d0a94cac6b0a2a5b1e
Source dataset
uspto-grants-1976_11
Patent number
US03992394

Reaction notes

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