Acetic Acid → HCID 22727100, compound

HRID 2086270Notes

Reaction equation

HRID 2086270 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]([NH:13][N:14]=[C:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=[O:12])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]([NH:13][NH:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)[CH2:17][CH2:16]1)=[O:12])[CH3:9])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 22727064HCID 22727064, compound

Product 1

HCID 22727100HCID 22727100, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The resultant 1-[(tert-butoxycarbonyl)sarcosinyl]-2-[1-(4-pyridyl)-4-piperidinylidene]hydrazine (1.0 g) was dissolved in methanol (20 ml) and treated with acetic acid (665 mg) with cooling on ice, followed by sodium cyanoborohydride (261 mg) and stirred at room temperature for 30 minutes. The reaction mixture was concentrated and the residue was dissolved in dichloromethane, washed with aqueous sodium bicarbonate and brine, dried and concentrated to obtain 1-[(tert-butoxycarbonyl)sarcosinyl]-2-[1-(4-pyridyl)-4-piperidinyl]hydrazine (1.0 g) as a colorless oil.

Workup

  1. temperaturewith cooling on ice
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with aqueous sodium bicarbonate and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-10e8ac9d6deb487bb8a629e480f5e315
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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