Potassium Carbonate → HCID 12804787, compound

HRID 1648923Notes

Reaction equation

HRID 1648923 reaction equation
Cl.[C:2]1([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[O:27]([CH2:34][CH2:35][CH2:36]Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(O)CCC>[O:27]([CH2:34][CH2:35][CH2:36][N:18]1[CH2:17][CH2:16][CH:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:20][CH2:19]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 12542646HCID 12542646, compound

Product 1

HCID 12804787HCID 12804787, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

4.40 g of 4-(α-phenyl-2-tolyl)piperidine hydrochloride of Example 35 and 14 g K2CO3 in 50 ml of n-butanol are heated to reflux with stirring. To this is added 5.66 g 3-phenoxypropylbromide in 10 ml of n-butanol dropwise. The mixture is then refluxed for 24 hours. After cooling the suspension is suction filtered, washing the flask and filter cake with n-butanol. The combined filtrates are evaporated to an oil which is dissolved in 20 ml of isopropanol and made acid with HCl/ether. The hydrochloride is collected by suction filtration and washed with ether. The resultant product is recrystallized from isopropanol/ether to yield 1-(3-phenoxypropyl)-4-(α-phenyl-2-tolyl)piperidine, mp 139°-140° C.

Workup

  1. temperatureto reflux
  2. temperatureThe mixture is then refluxed for 24 hours
  3. temperatureAfter cooling the suspension
  4. filtrationsuction filtered
  5. washwashing the flask
  6. filtrationfilter cake with n-butanol
  7. customThe combined filtrates are evaporated to an oil which
  8. dissolutionis dissolved in 20 ml of isopropanol
  9. filtrationThe hydrochloride is collected by suction filtration
  10. washwashed with ether
  11. customThe resultant product is recrystallized from isopropanol/ether

Sources & evidence

ORD record
ord-7e0c0852c0fd48fcb2d8cd376cb789de
Source dataset
uspto-grants-1983_11
Patent number
US04414219

Reaction notes

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