Water → HCID 57419566, compound

HRID 2353255Notes

Reaction equation

HRID 2353255 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 116877404-(4-Hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 57419566HCID 57419566, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(4-hydroxy-phenyl)-piperazin-1-carboxylic acid tert-butyl ester (278 mg, 1 mmol), bromomethyl-benzene (171 mg, 1 mmol) and K2CO3 (138 mg, 1 mmol) in DMF (3 mL) was stirred at rt for 24 h and then at 50° C. for 6 h, followed by addition of water (150 mL). The resulting solid was collected by filtration and washed with water to yield the desired compound (340 mg, 92%) as a white solid: MS (ESI) m/z 369 (M+H); 1H NMR (400 MHz, CDCl3) δ 1.48 (s, 9H), 3.01 (t, J=4.8 Hz, 4H), 3.57 (t, J=4.8 Hz, 4H), 5.02 (s, 2H), 6.87-6.93 (m, 4H), 7.33-7.44 (m, 5H).

Workup

  1. waitat 50° C. for 6 h
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-e791f4c3fee3417bb578e5caaca3716d
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

Loading…