1-Butanol → HCID 20338287, compound

HRID 1395806Notes

Reaction equation

HRID 1395806 reaction equation
Cl.[CH2:2]([N:9]([CH2:19][CH2:20][Cl:21])[C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([NH2:14])=[O:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[Na+].[Na+].[OH:28][C:29]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(O)CCC>C(Cl)(Cl)Cl>[ClH:21].[CH2:2]([N:9]([CH2:19][CH2:20][N:32]1[CH2:33][CH2:34][C:29]([OH:28])([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:30][CH2:31]1)[C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([NH2:14])=[O:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 10340Sodium CarbonateHCID 963874-Phenylpiperidin-4-olHCID 20338242HCID 20338242, compound

Product 1

HCID 20338287HCID 20338287, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 19.5 g 2-[Benzyl(2-chloroethyl)amino]benzamide hydrochloride, 15.75 g powdered anhydrous Na2CO3, 10.6 g 4-hydroxy-4-phenylpiperidine and 250 ml butanol was refluxed 20 hours, cooled and an equal volume of chloroform added. The mixture was filtered and the filtrate concentrated on the rotovap to dryness. The residue was dissolved in 500 ml ether, a little dry ice added, the mixture filtered and concentrated to dryness. The residue in 300 ml ether was treated with dry HC1 and filtered to give 15 g product.

Workup

  1. temperaturewas refluxed 20 hours
  2. temperaturecooled
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated on the rotovap to dryness
  5. dissolutionThe residue was dissolved in 500 ml ether
  6. additiona little dry ice added
  7. filtrationthe mixture filtered
  8. concentrationconcentrated to dryness
  9. additionThe residue in 300 ml ether was treated with dry HC1
  10. filtrationfiltered

Sources & evidence

ORD record
ord-1de9394dd11f4aceb7150afe9d9682c8
Source dataset
uspto-grants-1980_05
Patent number
US04205173

Reaction notes

Loading…