Ammonia → HCID 12783354, compound

HRID 2398731Notes

Reaction equation

HRID 2398731 reaction equation
[N:1]1([CH:7]([CH3:16])[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Mg].Br[C:19]1[C:24]([O:25][CH3:26])=[C:23]([CH3:27])[CH:22]=[C:21]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:20]=1.BrCCBr.Cl.N>C(OCC)C>[CH3:26][O:25][C:24]1[C:23]([CH3:27])=[CH:22][C:21]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:20][C:19]=1[C:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([OH:9])[CH:7]([N:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[CH3:16]

Participants

8

Reactant 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 458526HCID 458526, compoundHCID 5462224MagnesiumHCID 20517075HCID 20517075, compound

Product 1

HCID 12783354HCID 12783354, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

15 g of α-piperidinopropiophenone were added to a Grignard solution of 7.3 g of magnesium, 38.5 g of 6-bromo-2-methyl-4-tert-butylanisole and 28.2 g of 1,2,-dibromethane in 300 ml of diethyl ether. After boiling for 4 hours under reflux, the reaction mixture was poured on to ice and acidified with hydrochloric acid. The acidic aqueous solution and the oily intermediate layer were both separated, together made alkaline with a concentrated aqueous ammonia solution, and the base which separated therefrom was dissolved in diethyl ether. After evaporation of the diethyl ether, 26.5 g of a viscous brown oil were obtained from which, upon trituration of dilution with isopropanol, 21.5 g of 1-(2'-methoxy-3'-methyl-5'-tert-butylphenyl)-1-phenyl-2-piperidino-propan-1-ol, having a melting point of 86° C. to 87° C., crystallized out. The product was recrystallized from isopropanol and then had a melting point of 87° C. to 88° C.

Workup

  1. temperatureunder reflux
  2. additionthe reaction mixture was poured on to ice
  3. customthe base which separated
  4. dissolutiontherefrom was dissolved in diethyl ether
  5. customAfter evaporation of the diethyl ether

Sources & evidence

ORD record
ord-75b3ccc11583498788b7dba968041fde
Source dataset
uspto-grants-1977_05
Patent number
US04025633

Reaction notes

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