Water → 1-BOC-4-(2,4-difluorobenzyl)piperazine

HRID 639459Notes

Reaction equation

HRID 639459 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N:11]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.O>C(Cl)Cl>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][N:14]1[CH2:13][CH2:12][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 737702,4-DifluorobenzaldehydeHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 684130721-BOC-4-(2,4-difluorobenzyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,4-difluorobenzaldehyde (3.0 g, 21.1 mmol) and t-butyl piperazine-1-carboxylate (4.3 g, 23.1 mmol) in 30 mL of dry DCM is stirred for 2 h at RT, and NaHB(OAc)3 (6.7 g, 31.6 mmol) is added in portions with stirring. After the addition, the reaction mixture is stirred further overnight at RT. Water is added and the resulting mixture is extracted twice with DCM. The organic layer is dried over anhydrous MgSO4, filtered and concentrated in vacuo to obtain t-butyl 4-(2,4-difluorobenzyl)piperazine-1-carboxylate as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 1.46 (s, 9H), 2.40 (m, 4H), 3.42 (m, 4H), 3.54 (s, 2H), 6.78 (dt, 1H, J=10.0 Hz and 2.4 Hz), 6.85 (dt, 1H, J=8.4 Hz and 2.4 Hz), 7.33 (dd, 1H, J=15.2 Hz and 8.0 Hz).

Workup

  1. stirringwith stirring
  2. additionAfter the addition
  3. stirringthe reaction mixture is stirred further overnight at RT
  4. extractionthe resulting mixture is extracted twice with DCM
  5. dry with materialThe organic layer is dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13ac04fd19b34741b903df1a61d31b86
Source dataset
uspto-grants-2010_04
Patent number
US07691869B2

Reaction notes

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