Hydrochloric Acid → HCID 70361446, compound

HRID 2108205Notes

Reaction equation

HRID 2108205 reaction equation
Cl.[OH:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12]N(CCC)C2)[CH:6]=[CH:7][CH:8]=1.[C:18]([Cl:29])(=[O:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[N:30]1[CH:35]=C[CH:33]=[CH:32][CH:31]=1.Cl>ClCCl.CCOCC>[ClH:29].[C:18]([O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:35][N:30]2[CH2:31][CH2:32][CH3:33])[CH:6]=[CH:7][CH:8]=1)(=[O:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 66982Decanoyl chlorideHCID 1574713-(1-Propylpiperidin-3-yl)phenol--hydrogen chloride (1/1)

Product 1

HCID 70361446HCID 70361446, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

(-)-3-(3-hydroxyphenyl)-1-propylpiperidine hydrochloride (1.5 g, 5.86 mmol) was suspended in dry dichloromethane (15 ml). Decanoylchloride (1.2 g, 6.29 mmol) was dissolved in a mixture of dichloromethane (15 ml) and pyridine (0.5 g, 6.32 mmol). The solution was added to the suspension and the mixture was refluxed for 20 hours. The clear solution was cooled, washed with aqueous NaHCO3 and dried with Na2SO4. After evaporation the residual oil was dissolved in ether and precipitated as hydrochloride salt with one equivalent HCl in ether. The salt was recrystallized twice from acetone. Yield: 0.7 g (30%). M.p. 142°-144° C. [α]20D (C-1.8, MeOH)=-5.6° , MS (70 eV): m/z 373 (5%), 344 (100%), 190 (7%).

Workup

  1. additionThe solution was added to the suspension
  2. temperaturethe mixture was refluxed for 20 hours
  3. temperatureThe clear solution was cooled
  4. washwashed with aqueous NaHCO3
  5. dry with materialdried with Na2SO4
  6. customAfter evaporation the residual oil
  7. dissolutionwas dissolved in ether
  8. customThe salt was recrystallized twice from acetone
  9. customM.p. 142°-144° C. [α]20D (C-1.8, MeOH)=-5.6° , MS (70 eV)

Sources & evidence

ORD record
ord-87f597d90c89427a9817172375160a8b
Source dataset
uspto-grants-1990_06
Patent number
US04937346

Reaction notes

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