Hydrochloric Acid → HCID 68467974, compound

HRID 2235281Notes

Reaction equation

HRID 2235281 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10]1=[O:20].C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Cs+].[Cs+].Cl.Cl[CH2:42][CH2:43][N:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1.Cl.CCOCC>CC(C)=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:42][CH2:43][N:44]3[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]3)=[CH:25][CH:26]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[C:10]1=[O:20]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 59299341HCID 59299341, compound

Product 1

HCID 68467974HCID 68467974, compoundYield 196.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Charge a vial with 3-(3-chloro-4′-hydroxy-biphenyl-4-ylmethyl)-1-cyclohexyl-pyrrolidin-2-one (70 mg, 0.18 mmol) and dissolve in acetone (0.3 M). Add K2CO3 (250 mg, 1.8 mmol) and Cs2CO3 (59 mg, 0.18 mmol) and stir at room temperature for 5 minutes. Add 1-(2-chloro-ethyl)-piperidine hydrochloride (77 mg, 0.42 mmol) and heat to 50° C. overnight. Cool to room temperature, filter, concentrate and purify over silica gel. Dissolve the residue in methylene chloride (0.1 M) and add 2 M HCl in ether (0.18 mL, 0.36 mmol) and concentrate in vacuo to afford 94 mg (97%) of the title compound: Mass spectrum (apci) m/z=495.4 (M+H).

Workup

  1. filtrationfilter
  2. concentrationconcentrate
  3. custompurify over silica gel
  4. dissolutionDissolve the residue in methylene chloride (0.1 M)
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f912cd4ed1954a51ba9b455109915d85
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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