Hydrochloric Acid → HCID 22054643, compound

HRID 1829712Notes

Reaction equation

HRID 1829712 reaction equation
[N+](C1C=CC=CC=1O)([O-])=O.[C:11]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=O)=[CH:13][CH:12]=1.CC(C)N=C=NC(C)C.[N:36]1([CH:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)[CH2:40][CH2:39][CH2:38][CH2:37]1.[ClH:47]>ClCC(Cl)C.CN(C=O)C.C(O)C>[ClH:47].[C:11]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=[CH:13][C:14]([CH2:17][C:18]([N:44]2[CH2:45][CH2:46][CH:41]([N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH2:42][CH2:43]2)=[O:20])=[CH:15][CH:16]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 3332FelbinacHCID 69472-NitrophenolHCID 12734DiisopropylcarbodiimideHCID 787034-(1-Pyrrolidinyl)piperidine

Product 1

HCID 22054643HCID 22054643, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 65641,2-DichloropropaneSolvent3×

Procedure

To the polymeric nitrophenol (1.5 g, approx. 1 mmol) was added a filtered solution of 4-biphenylylacetic acid (1.10 g, 5.18 mmol) in a mixture of 1,2-dichloropropane (18 ml) and DMF (2 ml), followed by the addition of a solution of DIC (0.63 g, 4.99 mmol) in 1,2-dichloropropane (5 ml). The mixture was shaken at room temperature for 15 hours, filtered, and the polymer was extensively washed with DCM, DMF, and 1,2-dichloropropane. To the polymer was added 1,2-dichloropropane (5 ml) and a solution of 4-(1-pyrrolidinyl)piperidine (0.123 g, 0.80 mmol) in 1,2-dichloropropane (10 ml). The resulting mixture was shaken at room temperature for 21 hours and then at 60° C. for one hour, filtered, and the polymer was carefully washed with DCM and methanol. The combined filtrates were concentrated to yield the crude product, which was mixed with ethanol and 1 molar aqueous hydrochloric acid, concentrated, and the residual hydrochloride was recrystallized from ethanol. 90 mg (29%) of the title compound was obtained.

Workup

  1. filtrationfiltered
  2. washthe polymer was extensively washed with DCM, DMF, and 1,2-dichloropropane
  3. additionTo the polymer was added 1,2-dichloropropane (5 ml)
  4. stirringThe resulting mixture was shaken at room temperature for 21 hours
  5. waitat 60° C. for one hour
  6. filtrationfiltered
  7. washthe polymer was carefully washed with DCM and methanol
  8. concentrationThe combined filtrates were concentrated
  9. customto yield the crude product, which
  10. concentrationconcentrated
  11. customthe residual hydrochloride was recrystallized from ethanol

Sources & evidence

ORD record
ord-b088907e24a64a038b49f39512bc6ea8
Source dataset
uspto-grants-2006_06
Patent number
US07064135B2

Reaction notes

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