1-Acetylpiperazine → Tert-butyl 3-[(4-acetylpiperazin-1-yl)methyl]-5-methylphenylcarbamate

HRID 968245Notes

Reaction equation

HRID 968245 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:6]=[C:7]([CH3:9])[CH:8]=1)=O.[C:18]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(=[O:20])[CH3:19].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O.ClC(Cl)C.C([O-])(O)=O.[Na+]>[C:18]([N:21]1[CH2:26][CH2:25][N:24]([CH2:1][C:3]2[CH:4]=[C:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:6]=[C:7]([CH3:9])[CH:8]=2)[CH2:23][CH2:22]1)(=[O:20])[CH3:19]

Participants

7

Reactant 3

HCID 837951-Acetylpiperazine2×HCID 5049666Sodium triacetoxyborohydride2×HCID 22288418HCID 22288418, compound

Product 1

HCID 22288425Tert-butyl 3-[(4-acetylpiperazin-1-yl)methyl]-5-methylphenylcarbamate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl 3-formyl-5-methylphenylcarbamate (200 mg, 0.85 mmol) and acetylpiperazine (131 mg, 1.02 mmol) in 0.1 mL HOAc and 4 mL dichloroethane was added NaBH(OAc)3 (216 mg, 1.02 mmol) at room temperature. After 2 hours additional acetylpiperazine (131 mg, 1.02 mmol) and NaBH(OAc)3 (216 mg, 1.02 mmol) were added. After 2 hours the mixture was diluted with saturated NaHCO3. The layers were separated and the aqueous extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (5% MeOH/CH2Cl2) gave tert-butyl 3-[(4-acetylpiperazin-1-yl)methyl]-5-methylphenylcarbamate as a white foam:

Workup

  1. customThe layers were separated
  2. extractionthe aqueous extracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7ea9157a90f745ec8824265b942c1b79
Source dataset
uspto-grants-2005_10
Patent number
US06958340B2

Reaction notes

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