Hydrochloric Acid → 1-Cyclohexyl-4-[4-(2-methoxy-phenyl)-piperazin-1-YL]-2-phenyl-butan-1-one dihydrochloride

HRID 969953Notes

Reaction equation

HRID 969953 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]([C:25]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH2:11][CH2:10]1.[ClH:33].C(OCC)C>CO>[ClH:33].[ClH:33].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][C:17]([C:25]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:26])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH3:18])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 98029871-Cyclohexyl-4-(4-(2-methoxyphenyl)piperazin-1-yl)-2-methyl-2-phenylbutan-1-one

Product 1

HCID 222441101-Cyclohexyl-4-[4-(2-methoxy-phenyl)-piperazin-1-YL]-2-phenyl-butan-1-one dihydrochlorideYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(+)-1-(2-methoxyphenyl)-4-[3-(cyclohexanecarbonyl)-3-(phenyl)butyl]piperazine (15.0 g, 34.5 mmol, prepared above) was diluted with methanol (40 mL). To this solution was added HCl (9.58 g of a 26.3% solution in methanol, 69.0 mmol). The mixture began to form gelatinous-looking crystals and set up solid within minutes. To this mixture was added with vigorous stirring, diethyl ether (100 mL). The white solid was collected by suction filtration and then dried under vacuum at 45° C. for two days to provide the title compound (13.4 g, 76%) as a white solid; mp(DSC)=195.58° C.; IR (CDCl3, cm−1) 2976, 2939, 1700, 1502, 1462, 1451, 1267, 1243, 1021; 1H NMR (300 MHz, DMSO) δ 7.40 (2H, m), 73.1 (3H, m) 7.03 (3H, M) 6.90 (1H, m) 3.78 (3H, s) 3.49 (4H, m) 3.16 (5H, m) 2.64 (1H, m) 2.40 (3H, m) 1.56 (3H, s) 1.46 (4H, m) 1.1; (5H, m) 0.86 (1H, m); 13C NMR (300 MHz, DMSO) δ 213.46, 151.84, 139.56, 138.12, 128.72, 127.37, 126.86, 124.29, 120.85, 118.71, 112.29, 55.48, 54.06, 52.20, 50.78, 50.57, 46.93, 45.14, 30.31, 30.16, 25.15, 24.91, 24.89, 19.15; HRMS calcd for C28H39N2O2 (MH+) 435.3012, found 435.3018. [α]25D=+76.53° (c=1, MeOH), ee 99.3% (Chiral HPLC).

Workup

  1. customto form gelatinous-looking crystals
  2. filtrationThe white solid was collected by suction filtration
  3. customdried under vacuum at 45° C. for two days

Sources & evidence

ORD record
ord-fa400846ba24480b97a7c2512396f15f
Source dataset
uspto-grants-2007_12
Patent number
US07309702B2

Reaction notes

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