Acetaldehyde → cis-4-amino-5-chloro-N-(1-ethyl-3-methoxy-4-piperidinyl)-2-methoxybenzamide monohydrate

HRID 345595Notes

Reaction equation

HRID 345595 reaction equation
S1C=C[CH:3]=[CH:2]1.C(=[O:8])C.[NH2:9][C:10]1[C:26]([Cl:27])=[CH:25][C:13]([C:14]([NH:16][C@H:17]2[CH2:22][CH2:21][NH:20][CH2:19][C@H:18]2[O:23][CH3:24])=[O:15])=[C:12]([O:28][CH3:29])[CH:11]=1.[H][H]>O1CCCC1.[Pt].CO.C(O)C>[OH2:8].[NH2:9][C:10]1[C:26]([Cl:27])=[CH:25][C:13]([C:14]([NH:16][C@H:17]2[CH2:22][CH2:21][N:20]([CH2:2][CH3:3])[CH2:19][C@H:18]2[O:23][CH3:24])=[O:15])=[C:12]([O:28][CH3:29])[CH:11]=1

Participants

9

Reactant 4

HCID 177AcetaldehydeHCID 8030ThiopheneHCID 98616214-Amino-5-chloro-2-methoxy-N-[(3R,4S)-3-methoxypiperidin-4-YL]benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 67914529cis-4-amino-5-chloro-N-(1-ethyl-3-methoxy-4-piperidinyl)-2-methoxybenzamide monohydrate

Reagents, catalysts & solvents 4

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 1 part of a solution of 2 parts of thiophene in 40 parts of ethanol were added 12 parts of an acetaldehyde solution 10% in tetrahydrofuran, 6.3 parts of cis-4-amino-5-chloro-2-methoxy-N-(3-methoxy-4piperidinyl)benzamide and 120 parts of methanol. The whole was hydrogenated at normal pressure and at room temperature with 2 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was suspended in a mixture of 2,2'-oxybispropane and petroleumether. The product was filtered off and crystallized from acetonitrile. The product was filtered off and dried, yielding a first fraction of 2 parts of cis-4-amino-5-chloro-N-(1-ethyl-3-methoxy-4-piperidinyl)-2-methoxybenzamide monohydrate; mp. 130.2° C. The mother liquor was concentrated. A second fraction was filtered off, yielding 2.89 parts of cis-4-amino-5-chloro-N-(1-ethyl-3-methoxy-4-piperidinyl)-2-methoxybenzamide monohydrate; mp. 150.5° C. (compound 146).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additionThe residue was suspended in a mixture of 2,2'-oxybispropane and petroleumether
  4. filtrationThe product was filtered off
  5. customcrystallized from acetonitrile
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-11cacec566554905bad1451e0f77d566
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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