Hydrochloric Acid → HCID 19791688, compound

HRID 236409Notes

Reaction equation

HRID 236409 reaction equation
[NH2:1][CH:2]([CH2:11][CH:12]([CH3:14])[CH3:13])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[Cl:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[ClH:25]>C(O)C>[ClH:15].[ClH:25].[CH3:13][CH:12]([CH3:14])[CH2:11][CH:2]([NH:1][CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 79625Piperidine, 1-(3-chloropropyl)-HCID 13949648(1RS,2SR)-2-Amino-4-methyl-1-phenylpentan-1-ol

Product 1

HCID 19791688HCID 19791688, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (1RS,2SR)-2-amino-4-methyl-1-phenylpentane-1-ol (40.6 g, 210 mmol) and 1-(3-chloropropyl)piperidine (34.0 g, 210 mmol) was melted together at 50° to 70° C. in a nitrogen atmosphere. The mixture was then heated on an oil bath of 110° to 120° C. for 3 hours. After being cooled, the reaction mixture was dissolved with heating in ethanol (750 ml), followed by addition of concentrated hydrochloric acid (17 ml). The mixture was cooled and precipitated crystals were collected by filtration. The crystals were agian suspended in ethanol (1,200 ml) and heated under reflux for one hour. The mixture was cooled and the resulting crystals were collected by filtration, washed and then dried to obtain 58.8 g of the intended compound as white crystals [yield: 72%, m.p.: 268°-270° C. (decomposed)].

Workup

  1. customwas melted together at 50° to 70° C. in a nitrogen atmosphere
  2. temperatureThe mixture was then heated on an oil bath of 110° to 120° C. for 3 hours
  3. temperatureAfter being cooled
  4. dissolutionthe reaction mixture was dissolved
  5. temperatureThe mixture was cooled
  6. customprecipitated crystals
  7. filtrationwere collected by filtration
  8. temperatureheated
  9. temperatureunder reflux for one hour
  10. temperatureThe mixture was cooled
  11. filtrationthe resulting crystals were collected by filtration
  12. washwashed
  13. customdried

Sources & evidence

ORD record
ord-c5d5b832dbae4b10b742af9e4cb53d8d
Source dataset
uspto-grants-1987_02
Patent number
US04644063

Reaction notes

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