Sulfuric Acid → HCID 20299066, compound

HRID 1414915Notes

Reaction equation

HRID 1414915 reaction equation
S(=O)(=O)(O)O.[CH:6]1([N:12]2[CH2:16][CH2:15][CH:14]([C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:18]#[N:19])[CH2:13]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-:32].[NH4+]>C(OCC)(=O)C>[CH:6]1([N:12]2[CH2:16][CH2:15][CH:14]([C:17]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:18]([NH2:19])=[O:32])[CH2:13]2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 20299071HCID 20299071, compound

Product 1

HCID 20299066HCID 20299066, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To 80 ml. of concentrated sulfuric acid was added 20 g. (0.057 mole) of α-(cyclohexyl-3-pyrrolidinyl)-α,α-diphenylacetonitrile. The mixture was shaken until solution occurred while being cooled in an ice bath until heat was no longer evolved. The solution was heated at 70° C. for 48 hours, poured on ice and made basic with ammonium hydroxide. The resulting white solid precipitate was taken up in ethyl acetate and the solution dried over sodium sulfate. The solution was concentrated and the residual oil taken up in hot ligroin, filtered and allowed to stand overnight at room temperature. The resulting crystals were recrystallized from ligroin. Yield 9.0 g. (42.5%); m.p. 119°-121° C.

Workup

  1. temperaturewhile being cooled in an ice bath
  2. temperatureuntil heat
  3. additionpoured on ice
  4. dry with materialthe solution dried over sodium sulfate
  5. concentrationThe solution was concentrated
  6. filtrationfiltered
  7. customThe resulting crystals were recrystallized from ligroin

Sources & evidence

ORD record
ord-435ceea0b3294a9aab6fa763081b4309
Source dataset
uspto-grants-1977_01
Patent number
US04002766

Reaction notes

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