Triethylamine → 4-[2-(1-tert-Butoxycarbonyl-piperidin-4-yloxy)-phenyl]-piperazine-1-carboxylic acid benzyl ester

HRID 456469Notes

Reaction equation

HRID 456469 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN([CH2:32][CH3:33])CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([N:24]1[CH2:23][CH2:22][N:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH:11]2[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]2)[CH2:26][CH2:25]1)([O:3][CH2:4][C:33]1[CH:32]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 18436771HCID 18436771, compound

Product 1

HCID 184367864-[2-(1-tert-Butoxycarbonyl-piperidin-4-yloxy)-phenyl]-piperazine-1-carboxylic acid benzyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[2-(N-boc-piperidin-4-yloxy)-phenyl]-piperazine (1.5 g, 4.1 mol, 1.0 eq.) in DCM (20 mL) was added Et3N (0.8 mL, 5.74 mmol, 1.4 eq.), di-carbobenzoyloxy anhydride (1.4 g, 4.9 mmol, 1.2 eq.) and DMAP (25 mg, 0.2 mmol, 0.5 eq.). The mixture was stirred at r.t. overnight. The solution was diluted with DCM (100 mL) and washed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL). The organic layer was dried (Na2SO4), filtered and concentrated to afford the title compound (2.03 g, 4.1 mmol, 100%).

Workup

  1. washwashed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-23d3f7a848be41afa10b4de4d241eec5
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

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