Potassium Carbonate → HCID 66758232, compound

HRID 1983691Notes

Reaction equation

HRID 1983691 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH3:19])[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)([OH:11])[CH2:9][CH2:8][NH:7][CH2:6]1)=[O:4].C([O-])([O-])=O.[K+].[K+].Br[CH2:27][CH2:28][CH:29]=[C:30]1[C:36]2[CH:37]=[CH:38][CH:39]=[N:40][C:35]=2[CH2:34][O:33][C:32]2[CH:41]=[CH:42][C:43]([C:45]([OH:48])([CH3:47])[CH3:46])=[CH:44][C:31]1=2>C(#N)C.O>[CH3:1][O:2][C:3]([C:5]1([CH3:19])[C:10]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)([OH:11])[CH2:9][CH2:8][N:7]([CH2:27][CH2:28][CH:29]=[C:30]2[C:36]3[CH:37]=[CH:38][CH:39]=[N:40][C:35]=3[CH2:34][O:33][C:32]3[CH:41]=[CH:42][C:43]([C:45]([OH:48])([CH3:47])[CH3:46])=[CH:44][C:31]2=3)[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 666859992-[5-(3-Bromo-propylidene)-5,1 1-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-olHCID 66758385HCID 66758385, compound

Product 1

HCID 66758232HCID 66758232, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of 4-(4-chloro-phenyl)-4-hydroxy-3-methyl-piperidine-3-carboxylic acid methyl ester (0.71 g, 2.5 mmol) in acetonitrile/water (8:2) (25 mL) was added K2CO3 (1.40g, 10.0 mmol) and 2-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (0.937 g, 2.5 mmol). The solution was allowed to stir at room temperature for 48 h. The reaction was concentrated and partitioned between EtOAc/H2O, extracted with EtOAc (3×). The organics were collected together dried over Mg2SO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (50% ethyl acetate/50% hexane to 75% ethyl acetate/25% hexane to 100% ethyl acetate) to yield the title compound (0.835 g, 58%). 1H-NMR (CDCl3): 1.30 (s, 3H), 1.57 (s, 6H), 1.76 (d, 1H), 2.24-2.53 (m, 7H), 2.65 (d, 1H), 2.86 (d, 2H), 3.44 (s, 3H), 5.30 (bs, 2H), 6.16 (d, 1H), 6.82 (d, 1H), 7.26 (m, 4H), 7.45 (s, 1H), 7.53 (d, 1H), 7.58 (d, 1H), 8.49 (d, 1H). ESI-MS m/z: 577 (M+1), retention time 1.50.

Workup

  1. concentrationThe reaction was concentrated
  2. custompartitioned between EtOAc/H2O
  3. extractionextracted with EtOAc (3×)
  4. customThe organics were collected together
  5. dry with materialdried over Mg2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. custompurified by Biotage flash chromatography (50% ethyl acetate/50% hexane to 75% ethyl acetate/25% hexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-25c166c15002497f9476c23a9924af9b
Source dataset
uspto-grants-2009_06
Patent number
US07541365B2

Reaction notes

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