Nitrate → 4-Nitroxymethylpiperidine nitrate

HRID 1198139Notes

Reaction equation

HRID 1198139 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[N+:9]([O-:12])([OH:11])=[O:10].[N+:13]([O-])([O:15]C(=O)C)=[O:14].C(OC(C)C)(C)C.[N+]([O-])([O-])=O>C(#N)C>[N+:9]([O-:12])([OH:11])=[O:10].[O:1]([CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[N+:13]([O-:15])=[O:14]

Participants

7

Reactant 5

HCID 943NitrateHCID 944Nitric Acid2×HCID 7914Diisopropyl EtherHCID 11557Acetyl nitrateHCID 4207714-Piperidinemethanol

Product 1

HCID 532305974-Nitroxymethylpiperidine nitrate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.8 g. 4-Hydroxymethylpiperidine are dissolved in 100 ml. acetonitrile and cooled to -25° C. By the addition of 3.1 ml. 100% nitric acid, the base is converted into the nitric acid salt. To this solution is added a freshly prepared acetyl nitrate solution (prepared from 9.5 ml. acetic anhydride and 4.2 ml. 100% nitric acid in 40 ml. acetonitrile at -25° C.) and the reaction mixture then stirred for 3 hours at this temperature. The reaction solution is diluted with 300 ml. diisopropyl ether. The crystals obtained are filtered off with suction and washed with diethyl ether. There are obtained 9.5 g. (82% of theory) of the nitrate of the title compound; m.p. 64°-65° C.

Workup

  1. additionBy the addition of 3.1 ml
  2. additionThe reaction solution is diluted with 300 ml
  3. customThe crystals obtained
  4. filtrationare filtered off with suction
  5. washwashed with diethyl ether
  6. customThere are obtained 9.5 g

Sources & evidence

ORD record
ord-59e0597814a94e92a9f39cdaaad05ad4
Source dataset
uspto-grants-1994_01
Patent number
US05280031

Reaction notes

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