Aniline → N-(((2S)-1,4-dibenzyl-2-piperazinyl)methyl)aniline

HRID 1972614Notes

Reaction equation

CS(O[CH2:6][C@H:7]1[CH2:12][N:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9][N:8]1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=O)=O.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CO>[CH2:20]([N:8]1[CH2:9][CH2:10][N:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][C@@H:7]1[CH2:6][NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A 20-mL vial was charged ((2R)-1,4-dibenzyl-2-piperazinyl)methyl methanesulfonate (1.01 g, 2.70 mmol, Example 184, Step 1), aniline (1.30 mL, 14.3 mmol, Alfa Aesar, Ward Hill, Mass.) and MeOH (12 mL). The reaction mixture was sealed and heated at 140° C. for 30 min in an Initiator microwave reactor (Biotage AB, Inc., Uppsala, Sweden). The mixture was allowed to cool to room temperature and then concentrated in vacuo. The crude product was purified by column chromatography (50 g of silica gel, (2 M NH3 in MeOH) in CH2Cl2 0 to 5%) to afford N-(((2S)-1,4-dibenzyl-2-piperazinyl)methyl)aniline (0.734 g) as an orange oil.

Workup

customThe reaction mixture was sealed
temperatureto cool to room temperature
concentrationconcentrated in vacuo
customThe crude product was purified by column chromatography (50 g of silica gel, (2 M NH3 in MeOH) in CH2Cl2 0 to 5%)

Sources & evidence

ORD record: ord-7c5d0a86eba341358c58c8bc608791cc
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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