4-Bromobenzaldehyde → Phenylmethyl (2S)-4-[(4-bromophenyl)methyl]-2-methyl-1-piperazine Carboxylate

HRID 43340

Reaction equation

HRID 43340 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C@H:11]1[CH2:16][NH:15][CH2:14][CH2:13][N:12]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:15]2[CH2:14][CH2:13][N:12]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[C@@H:11]([CH3:10])[CH2:16]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 707414-BromobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 40425199Benzyl (2S)-2-methylpiperazine-1-carboxylate

Product 1

HCID 25224210Phenylmethyl (2S)-4-[(4-bromophenyl)methyl]-2-methyl-1-piperazine CarboxylateYield 84.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-bromobenzaldehyde (1.19 g, 6.42 mmol), phenylmethyl (2S)-2-methyl-1-piperazinecarboxylate (1.505 g, 6.42 mmol) and sodium triacetoxyborohydride (2.04 g, 9.63 mmol) in 1,2-DCE (15 ml) was stirred at room temperature overnight. Saturated aq. NaHCO3 solution was added and the mixture stirred for 30 mins. Product was extracted and the extracts dried (Na2SO4). Chromatography (0-30% EtOAc in pentane) gave the title compound (2.18 g). MS (ES): MH+ 403/405.

Workup

  1. stirringthe mixture stirred for 30 mins
  2. extractionProduct was extracted
  3. dry with materialthe extracts dried (Na2SO4)

Sources & evidence

ORD record
ord-d3f1cc6cc426466f9662703f3e0ae627
Source dataset
uspto-grants-2013_09
Patent number
US08536182B2

Linked notes

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