Sodium Chloride → Ammonia

HRID 2166075Notes

Reaction equation

HRID 2166075 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH:2]1[CH2:7][OH:8].[C:9](OC(=O)C)(=[O:11])[CH3:10].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>O.C(N(CC)CC)C>[NH3:1].[C:9]([N:4]1[CH2:5][CH2:6][NH:1][CH:2]([CH2:7][OH:8])[CH2:3]1)(=[O:11])[CH3:10]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 11788288(Piperazin-2-yl)methanol

Product 2

HCID 222AmmoniaHCID 198967541-[3-(Hydroxymethyl)piperazin-1-yl]ethan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 2-piperazinemethanol (197 mg) and triethylamine (0.35 ml, 0.26 g) in water (4 ml) was treated with a mixture of acetic anhydride (0.16 ml) and water (1.5 ml) and was stirred at room temperature for 2 h. The solution was basified with sodium carbonate solution (2N, 1 ml), saturated with sodium chloride (1 g) and washed with dichloromethane (10 ml). The aqueous phase was evaporated in vacuo to give a solid which was purified by flash column chromatography eluting with dichloromethane:methanol:ammonia, (75:10:1.5) to give the title compound as an oil (188 mg).

Workup

  1. washwashed with dichloromethane (10 ml)
  2. customThe aqueous phase was evaporated in vacuo
  3. customto give a solid which
  4. customwas purified by flash column chromatography
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-0ce8ae53d3434736a1d2325ee455b69f
Source dataset
uspto-grants-1990_07
Patent number
US04943578

Reaction notes

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