tert-Butyl piperazine-1-carboxylate → HCID 89838038, compound

HRID 1771146Notes

Reaction equation

HRID 1771146 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].[CH3:14][CH:15]([CH3:28])[CH2:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][C:19]=1[O:26][CH3:27].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C([O-])(O)=O.[Na+]>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([O:17][CH2:16][CH:15]([CH3:14])[CH3:28])=[C:19]([O:26][CH3:27])[CH:20]=2)[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 6736974-isobutoxy-3-methoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 89838038HCID 89838038, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
20 °C

Procedure

The synthesis is carried out in argon condition. 2.2 g (11.8 mmol) of N-Boc-piperazine and 2.5 g (about 12 mmol) of crude 4-(2-methylpropyloxy)-3-methoxybenzaldehyde are mixed in 50 ml of dry of dichloromethane. After dissolution 2 drops of acetic acid is added, then 4.25 g (20 mmol) of NaBH(OAc)3 is added and the mixture is stirred for 12 h at 20° C. Then 20 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, concentrated in vacuum at 50÷80° C. The residue (3.3 g of oil)-crude N-(tert-butyloxycarbonyl)-N′-(4-(2-methylpropyloxy)-3-methoxybenzyl)piperazine is used on the next step without further purification.

Workup

  1. dry with materialof dry of dichloromethane
  2. dissolutionAfter dissolution 2 drops of acetic acid
  3. additionis added
  4. customThe organic layer is separated
  5. washwashed with 5% Na2CO3 solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered off
  8. concentrationconcentrated in vacuum at 50÷80° C
  9. customThe residue (3.3 g of oil)-crude N-(tert-butyloxycarbonyl)-N′-(4-(2-methylpropyloxy)-3-methoxybenzyl)piperazine is used on the next step without further purification

Sources & evidence

ORD record
ord-c725a1497fa84fa3b905ed8b4084a823
Source dataset
uspto-grants-2016_02
Patent number
US09249115B2

Reaction notes

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