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Acetic Acid → HCID 18959455, compound

HRID 1708536
Notes
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Reaction equation

HRID 1708536 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([Cl:11])=[CH:4][C:3]=1[CH2:12][CH:13]=O.C(O)(=O)C.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:11][C:5]1[CH:4]=[C:3]([CH2:12][CH2:13][N:29]2[CH2:28][CH2:27][N:26]([C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])[CH2:31][CH2:30]2)[C:2]([Cl:1])=[CH:7][C:6]=1[N+:8]([O-:10])=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 54165010HCID 54165010, compound

Product 1

HCID 18959455HCID 18959455, compound

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A methylene chloride solution of the title compound of Example 10 was stirred at room temperature under nitrogen. Acetic acid (8.8 ml, 153 mmol) was added in one portion followed by t-butylpiperazinecarboxylate (8.4 g, 50 mmol). Sodium triacetoxy-borohydride (16.2 g, 77 mmol) was added in portions as a solid and the reaction mixture stirred at room temperature for three hours. The reaction mixture was washed two times with excess saturated sodium carbonate solution and one time each with water and brine. The organic layer was dried over magnesium sulfate, filtered and evaporated to afford the title product as an oil 15.6 g, (98% crude yield). This was suitable for use in the next reaction without further purification. NMR (CDCl3) δ 7.92 (s, 1), 7.48 (s, 1), 3.43 (m, 4), 2.97 (t, 2), 2.62 (t, 2), 2.49 (m, 4), 1.43 (s, 9).

Workup

  1. washThe reaction mixture was washed two times with excess saturated sodium carbonate solution and one time each with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-89c4c92f3b1647c4b96e3c0345131622
Source dataset
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05359068

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes