Ammonia → HCID 67822513, compound

HRID 1741774Notes

Reaction equation

HRID 1741774 reaction equation
Cl[CH2:2][N:3]1[CH2:8][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][C:4]1=[O:21].[NH3:22].C1(C)C=CC=CC=1.[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34]>C(O)C.CCOCC.C1COCC1>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34].[NH2:22][CH2:2][N:3]1[CH2:8][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][C:4]1=[O:21]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 1140TolueneHCID 444266Maleic AcidHCID 15224690HCID 15224690, compound

Product 1

HCID 67822513HCID 67822513, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Chloromethyl-5,5-diphenyl-2-piperidinone (16g) was added portionwise over 15 min. to a mixture of ammonia (100 ml), toluene (100 ml) and THF (100 ml) at -40° C. with stirring and the mixture was allowed to warm to room temperature over 3 days. The reaction mixture was partitioned between water and chloroform and the combined organic solvents were washed with water and brine. Concentration of the solvents to dryness gave 15 g of crude product which was dissolved in absolute ethanol (150 ml) and treated with maleic acid (6 g) dissolved in ethanol (15 ml). Ether (50 ml) was added and the precipitated solid (13 g) was filtered off. The solid (13 g) was dissolved in 850 ml. of 40° C. water, filtered and the aqueous solution was freeze-dried to give the title product as a maleate salt (mp 136° C.).

Workup

  1. customThe reaction mixture was partitioned between water and chloroform
  2. washthe combined organic solvents were washed with water and brine
  3. customConcentration of the solvents to dryness gave 15 g of crude product which
  4. filtrationthe precipitated solid (13 g) was filtered off
  5. dissolutionThe solid (13 g) was dissolved in 850 ml
  6. filtrationof 40° C. water, filtered
  7. customthe aqueous solution was freeze-dried

Sources & evidence

ORD record
ord-333a9262d5134c38a4a1b105eaf630f9
Source dataset
uspto-grants-1994_08
Patent number
US05334720

Reaction notes

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