Water → HCID 70565949, compound

HRID 126909Notes

Reaction equation

HRID 126909 reaction equation
[NH2:1][C@@H:2]1[CH2:6][N:5]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:4][C@H:3]1[OH:13].C(=O)([O-])[O-].[K+].[K+].[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1.O>O1CCOCC1>[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:1][C@H:2]2[C@H:3]([OH:13])[CH2:4][N:5]([CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]3)[CH2:6]2)=[O:26])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 85014-Chlorobenzoyl chlorideHCID 11430Potassium CarbonateHCID 70564014HCID 70564014, compound

Product 1

HCID 70565949HCID 70565949, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 36.8 g of trans-4-amino-1-cyclohexyl-3-pyrrolidinol in 600 ml of p-dioxane was mixed with 40 g of powdered anhydrous potassium carbonate and stirred while 35.0 g of p-chlorobenzoyl chloride in 100 ml of p-dioxane was added dropwise. The mixture was stirred at room temperature for 2 hrs, then heated at reflux for 2 hrs. While still hot, 10 ml of water was added to make the precipitate granular; the mixture was filtered and the dioxane reduced to one-half volume. This solution was poured into one liter of water. The precipitate was collected and recrystallized from acetone. Yield was 60.5 g (94%), m.p. 193°-195° C.

Workup

  1. additionwas added dropwise
  2. temperatureheated
  3. temperatureat reflux for 2 hrs
  4. filtrationthe mixture was filtered
  5. additionThis solution was poured into one liter of water
  6. customThe precipitate was collected
  7. customrecrystallized from acetone

Sources & evidence

ORD record
ord-17e8b8e8bde64f36b389229f2065deb7
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

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