Hydrochloric Acid → HCID 131720059, compound

HRID 362736Notes

Reaction equation

HRID 362736 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:31][CH2:32]OS(C)(=O)=O)[CH2:14][N:13]([CH2:15][C:16]3[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=3)[C:12](=[O:30])[CH2:11][O:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[N:38]1([CH:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.O.[ClH:51]>CN(C=O)C.CCOCC>[OH2:10].[ClH:51].[ClH:51].[F:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:31][CH2:32][N:47]3[CH2:48][CH2:49][CH:44]([N:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[CH2:45][CH2:46]3)[CH2:14][N:13]([CH2:15][C:16]3[CH:21]=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:19]=[C:18]([C:26]([F:27])([F:29])[F:28])[CH:17]=3)[C:12](=[O:30])[CH2:11][O:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[F:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:31][CH2:32][N:47]3[CH2:48][CH2:49][CH:44]([N:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[CH2:45][CH2:46]3)[CH2:14][N:13]([CH2:15][C:16]3[CH:21]=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:19]=[C:18]([C:26]([F:27])([F:29])[F:28])[CH:17]=3)[C:12](=[O:30])[CH2:11][O:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[ClH:51].[ClH:51]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 786071,4'-BipiperidineHCID 21200578HCID 21200578, compound

Product 1

HCID 131720059HCID 131720059, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 0.86 g of the compound obtained in step C of EXAMPLE 26 and 0.7 g of 4-(piperid-1-yl)-piperidine in 3 ml of DMF is heated at 70° C. for 4 hours 30 minutes. After cooling to RT, the reaction mixture is poured into water and extracted with AcOEt, the organic phase is washed with 1N NaOH solution and with saturated NaCl solution and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica H using DCM and then a DCM/MeOH mixture (90/10; v/v) as the eluent. The product obtained is taken up with a saturated solution of hydrochloric acid in ether and the precipitate formed is wrung to give 0.49 g of the expected product. M.p.=260° C. (dec.).

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with AcOEt
  3. washthe organic phase is washed with 1N NaOH solution and with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica H
  7. customThe product obtained
  8. customthe precipitate formed

Sources & evidence

ORD record
ord-f8128c5f862c4a90aca4273e4b74d4c3
Source dataset
uspto-grants-1999_02
Patent number
US05869663

Reaction notes

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