Hydrochloric Acid → N-(7-hydroxy-5,6-dihydro-7H-cyclopenta[d]pyrimidin-4-yl)-4-[3-(1-benzylpiperidin-4-yl)propanoyl]aniline

HRID 976136Notes

Reaction equation

HRID 976136 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([C:18]2[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=2)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:28][CH:29]1[C:33]2[N:34]=[CH:35][N:36]=[C:37](Cl)[C:32]=2[CH2:31][CH2:30]1)(=O)C.Cl.C[O-].[Na+].CO>C(O)C>[OH:28][CH:29]1[C:33]2[N:34]=[CH:35][N:36]=[C:37]([NH:22][C:21]3[CH:20]=[CH:19][C:18]([C:16](=[O:17])[CH2:15][CH2:14][CH:11]4[CH2:12][CH2:13][N:8]([CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[CH2:9][CH2:10]4)=[CH:24][CH:23]=3)[C:32]=2[CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 199689194-[3-(1-Benzylpiperidin-4-yl)propanoyl]anilineHCID 199689354-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl acetateHCID 23694274Sodium methanolate methanol

Product 1

HCID 19968940N-(7-hydroxy-5,6-dihydro-7H-cyclopenta[d]pyrimidin-4-yl)-4-[3-(1-benzylpiperidin-4-yl)propanoyl]anilineYield 57.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 15 ml of ethanol were added 0.60 g of 4-[3-(1-benzylpiperidin-4-yl)propanoyl]aniline and 0.51 g of 7-acetoxy-4-chloro-5,6-dihydro-7H-cyclopenta[d]pyrimidine, then 3 ml of an ethanol solution of hydrochloric acid (containing 0.19 g of hydrochloric acid) was added to the mixture and the mixture was reacted under reflux for 30 minutes. After cooling, a 28% sodium methylate-methanol solution was added to the reaction mixture to make it alkaline, and the mixture was condensed under reduced pressure. The obtained residue was applied to silica gel column chromatography to obtain 0.49 g of the title compound as white crystal.

Workup

  1. customthe mixture was reacted
  2. temperatureunder reflux for 30 minutes
  3. temperatureAfter cooling
  4. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-28ec64a23db74abfbf55781afeece2a5
Source dataset
uspto-grants-1997_03
Patent number
US05610303

Reaction notes

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