Potassium Carbonate → tert-Butyl (+)-(1-{2-[4-Benzoyl-2-(3,4-difluorophenyl)morpholin-2-yl]ethyl}-4-phenylpiperid-4-yl)carbamate

HRID 1937036Notes

Reaction equation

HRID 1937036 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[C:8]1([C:14]2([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:28]([N:36]1[CH2:41][CH2:40][O:39][C:38]([C:54]2[CH:59]=[CH:58][C:57]([F:60])=[C:56]([F:61])[CH:55]=2)([CH2:42][CH2:43]OS(C2C=CC=CC=2)(=O)=O)[CH2:37]1)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O.C(#N)C>[C:28]([N:36]1[CH2:41][CH2:40][O:39][C:38]([CH2:42][CH2:43][N:17]2[CH2:18][CH2:19][C:14]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:15][CH2:16]2)([C:54]2[CH:59]=[CH:58][C:57]([F:60])=[C:56]([F:61])[CH:55]=2)[CH2:37]1)(=[O:35])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11179272(+)-4-Benzoyl-2-(3,4-difluorophenyl)-2-(2-benzenesulfonyloxyethyl)morpholineHCID 86758087Tert-butyl (4-phenylpiperid-4-yl)carbamate hydrochloride2×

Product 1

HCID 9916832tert-Butyl (+)-(1-{2-[4-Benzoyl-2-(3,4-difluorophenyl)morpholin-2-yl]ethyl}-4-phenylpiperid-4-yl)carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 18 g of potassium carbonate in 18 ml of water is added to a mixture of 22.6 g of tert-butyl (4-phenylpiperid-4-yl)carbamate hydrochloride (compound (IV)) and 30 g of compound of formula (III) obtained in Example 1 in 300 ml of acetonitrile, and the mixture is then heated at 70° C. for 12 hours and left overnight at room temperature. The acetonitrile is concentrated under vacuum, the residue is taken up in 300 ml of dichloromethane, the organic phase is washed successively with 150 ml of a 0.3 M solution of sodium hydroxide in water, with 150 ml of water, twice with 150 ml of pH 2 sulfate buffer, with 150 ml of water and with 150 ml of a 10% by weight solution of potassium carbonate in water, dried over magnesium sulfate and filtered, and the solvent is evaporated off under vacuum at room temperature. The expected product is obtained, which is used in Example 3.

Workup

  1. concentrationThe acetonitrile is concentrated under vacuum
  2. washthe organic phase is washed successively with 150 ml of a 0.3 M solution of sodium hydroxide in water, with 150 ml of water, twice with 150 ml of pH 2 sulfate buffer, with 150 ml of water and with 150 ml of a 10% by weight solution of potassium carbonate in water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent is evaporated off under vacuum at room temperature

Sources & evidence

ORD record
ord-ce307eb3c7754bd1af7dce4a914f4fc8
Source dataset
uspto-grants-2002_05
Patent number
US06392039B1

Reaction notes

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