Sulfuric Acid → HCID 67922715, compound

HRID 1110401Notes

Reaction equation

HRID 1110401 reaction equation
[NH2:1][C:2]1[C:33]([Cl:34])=[CH:32][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]([N:20]3[CH2:29][CH2:28][C:23]4(OCC[O:24]4)[CH2:22][CH2:21]3)=[O:19])[CH2:11][C@H:10]2[O:30][CH3:31])=[O:7])=[C:4]([O:35][CH3:36])[CH:3]=1.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O>[NH2:1][C:2]1[C:33]([Cl:34])=[CH:32][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18](=[O:19])[N:20]3[CH2:21][CH2:22][C:23](=[O:24])[CH2:28][CH2:29]3)[CH2:11][C@H:10]2[O:30][CH3:31])=[O:7])=[C:4]([O:35][CH3:36])[CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 67922661HCID 67922661, compound

Product 1

HCID 67922715HCID 67922715, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.1 parts of cis-4-amino-5-chloro-N-[1-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-4-oxobutyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide, 0.74 parts of sulfuric acid and 40 parts of water was stirred for 2 hours at reflux temperature. After cooling, the reaction mixture was made alkaline with sodium carbonate while cooling. The product was extracted with trichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried in vacuo at 60° C., yielding 1 part (51.9%) of cis-4-amino-5-chloro-2-methoxy-N-[3-methoxy-1-[4-oxo-4-(4-oxo-1-piperidinyl)butyl]-4-piperidinyl]benzamide; mp. 156.9° C. (compound 109).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. temperaturewhile cooling
  4. extractionThe product was extracted with trichloromethane
  5. washThe extract was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was crystallized from acetonitrile
  10. filtrationThe product was filtered off
  11. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-9d1bd1e56c0c46e38cc54e87460972be
Source dataset
uspto-grants-1990_12
Patent number
US04975439

Reaction notes

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