tert-Butyl piperazine-1-carboxylate → HCID 89838520, compound

HRID 1771139Notes

Reaction equation

HRID 1771139 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:14]([O:16][C:17]1[C:24]([O:25][CH2:26][CH3:27])=[C:23]([O:28][CH2:29][CH3:30])[CH:22]=[CH:21][C:18]=1[CH:19]=O)[CH3:15].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCl.C(O)(=O)C>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:19][C:18]2[CH:21]=[CH:22][C:23]([O:28][CH2:29][CH3:30])=[C:24]([O:25][CH2:26][CH3:27])[C:17]=2[O:16][CH2:14][CH3:15])[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 19956854Benzaldehyde, 2,3,4-triethoxy-

Product 1

HCID 89838520HCID 89838520, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

The synthesis is carried out in argon condition. 1.1 g (5.9 mmol) of N-Boc-piperazine and 1.40 g (5.9 mmol) of 2,3,4-triethoxybenzaldehyde are mixed in 25 ml of dry dichloromethane. After dissolution 2 drops of acetic acid is added, then 2.12 g (10 mmol) of NaBH(OAc)3 is added and the mixture is stirred for 12 h at 20° C. Then 10 ml of 5% NaHCO3 aqueous solution is added dropwise with care to the reaction mixture. The organic layer is separated, washed with 5% Na2CO3 solution, dried over sodium sulfate, filtered off and concentrated in vacuum at 50÷80° C. The residue (2.2 g of yellowish oil) is used on the next step.

Workup

  1. additionis added
  2. customThe organic layer is separated
  3. washwashed with 5% Na2CO3 solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated in vacuum at 50÷80° C

Sources & evidence

ORD record
ord-d62b6eb34aa44fea8b6513ab94e67292
Source dataset
uspto-grants-2016_02
Patent number
US09249115B2

Reaction notes

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