Water → 1-[3,3-Bis-(2-pyridyl)propyl]-4-(2-methoxyphenyl)piperazine

HRID 2181636Notes

Reaction equation

C([C:3]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH2:8][CH2:7]1)#N.S(=O)(=O)(O)O.O.[OH-].[Na+]>C(OCC)(=O)C>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH:3]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH2:8][CH2:7]1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 2.44 g of compound of Example 6 and 12 mL of 70% sulphuric acid was stirred for 1.5 h at 125° C. The obtained reaction mixture was then cooled to room temperature, followed by careful pouring into 100 g of ice, dilution with water, alkalinization with 35% sodium hydroxide, and extraction with ethyl acetate (3×40 mL). The combined organic phases were then washed with water, dried on anhydrous sodium sulphate, and then evaporated to complete dryness under vacuum. The obtained crude was then purified by flash chromatography (ethyl acetate-2.2 N solution of ammonia in methanol 9.6:0.4). The recovered fractions were then evaporated to complete dryness, affording 1.87 g of the title product (82%).

Workup

customThe obtained reaction mixture
temperaturewas then cooled to room temperature
washThe combined organic phases were then washed with water
dry with materialdried on anhydrous sodium sulphate
customevaporated
customThe obtained crude
customwas then purified by flash chromatography (ethyl acetate-2.2 N solution of ammonia in methanol 9.6:0.4)
customThe recovered fractions were then evaporated

Sources & evidence

ORD record: ord-1e3c101444d14e41be438836aa3dfe43
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06894052B1

Reaction notes

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