Piperidine-1-propylamine → HCID 67948145, compound

HRID 704826Notes

Reaction equation

HRID 704826 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:18][C:19]([O:21]CC)=[O:20])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C(N(C(C)C)CC)(C)C>CCOCC>[OH2:20].[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:18][C:19]([NH:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:21])[C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:18][C:19]([NH:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:21])[C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 19049Piperidine-1-propylamineHCID 81531DiisopropylethylamineHCID 146995514,5-Diphenyl-1-(ethoxycarbonylmethyl)-pyrazole

Product 1

HCID 67948145HCID 67948145, compoundYield 150.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 15 g (0.049 mol) of ethyl 4,5-diphenyl-1H-pyrazole-1-acetate of Example 1, 10.2 g (0.02 mol) of 3-aminopropylpiperidine, and 62 mL of diisopropylethylamine was stirred on a steam bath under nitrogen for 18 hours. The excess amine was stripped in vacuo. The residue was taken up in about 300 mL of ether and washed twice with water. The product was extracted into 150 mL of cold water containing 18 mL of 10% hydrochloric acid. The water layer was washed two times with ether, treated with decolorizing carbon, filtered, chilled and made basic with solid sodium carbonate. The product was extracted into methylene dichloride, dried over sodium sulfate, filtered, and stripped to 14.7 g of solid residue. The residue was triturated in water, filtered and dried to yield 12.36 g of 4,5-diphenyl-N-[3-(1-piperdinyl)propyl]-1H-pyrazole-1-acetamide hemihydrate, mp 81°-85° C.

Workup

  1. washwashed twice with water
  2. extractionThe product was extracted into 150 mL of cold water containing 18 mL of 10% hydrochloric acid
  3. washThe water layer was washed two times with ether
  4. additiontreated with decolorizing carbon
  5. filtrationfiltered
  6. temperaturechilled
  7. extractionThe product was extracted into methylene dichloride
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customThe residue was triturated in water
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-75c8ac70d492403db46bbf5c2b9e1f7c
Source dataset
uspto-grants-1991_01
Patent number
US04988725

Reaction notes

Loading…