1-Methylpiperazine → t-Butyl (1R)-1-(4-(2-methylpentyloxy)phenyl)-2-(4-methylpiperazin-1-yl)ethylcarbamate

HRID 1874635Notes

Reaction equation

HRID 1874635 reaction equation
[CH3:1][CH:2]([CH2:22][CH2:23][CH3:24])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=O)=[CH:7][CH:6]=1.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C>[CH3:1][CH:2]([CH2:22][CH2:23][CH3:24])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:12][N:29]2[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 531671-Methylpiperazine2×HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 86658401t-butyl (1R)-1-(4-(2-methylpentyloxy)phenyl)-2-oxoethylcarbamate

Product 1

HCID 67430949t-Butyl (1R)-1-(4-(2-methylpentyloxy)phenyl)-2-(4-methylpiperazin-1-yl)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of t-butyl (1R)-1-(4-(2-methylpentyloxy)phenyl)-2-oxoethylcarbamate (80 mg, 0.238 mmol) in dichloroethane (1 mL) was added 1-methylpiperazine (0.032 mL, 0.286 mmol) followed by sodium triacetoxyborohydride (70.8 mg, 0.334 mmol). The mixture was stirred at room temperature for 3 h. Additional 1-methylpiperazine (0.064 mL, 0.572 mmol) and sodium triacetoxyborohydride (71 mg, 0.334 mmol) were added and the mixture was stirred at room temperature for 1 h. The reaction mixture was transferred to a separatory funnel containing saturated aqueous NaHCO3 solution (5 mL). The aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (5 mL), dried over MgSO4, filtered and concentrated. The product, t-butyl 1-(4-(2-methylpentyloxy)phenyl)-2-(4-methylpiperazin-1-yl)ethylcarbamate, was used directly in the next step: LRMS (ESI) m/e 420.3 [(M+H)+, calcd for C24H42N3O3 420.3].

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. customThe reaction mixture was transferred to a separatory funnel
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×10 mL)
  4. washThe combined organic layers were washed with brine (5 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0ee0e807cfc94da6b739e2de1bd083ea
Source dataset
uspto-grants-2012_11
Patent number
US08304577B2

Reaction notes

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