Potassium Cyanide → HCID 44243001, compound

HRID 1013089Notes

Reaction equation

HRID 1013089 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[C:8]=1[C:16]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)=[O:17])=[O:5])[CH3:2].[NH4+:25].[Cl-].[C-:27]#[N:28].[K+]>CO>[NH2:25][C:21]1([C:27]#[N:28])[CH2:20][CH2:19][N:18]([C:16]([C:8]2[C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][C:7]=2[NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[O:17])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 25517Ammonium ChlorideHCID 57908080HCID 57908080, compound

Product 1

HCID 44243001HCID 44243001, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6B (1.0 equivalent) in MeOH (0.06M), was slowly added NH4Cl (1.2 equivalents) and 30% aq. NH3OH (0.06M) and stirred at room temperature for 30 minutes. The mixture was cooled at 0° C., and KCN was added in portions. After 12 hrs, 80% of MeOH was removed under reduced pressure, and then replaced MeOH with diethyl ether at 0° C. Filtered crystallized solid and washed crystals with cold diethyl ether twice to afford the 1-(3-(4-amino-4-cyanopiperidine-1-carbonyl)benzo[b]thiophen-2-yl)-3-ethylurea (6, 79%). Two rotamers observed (ratio 1:1).

Workup

  1. temperatureThe mixture was cooled at 0° C.
  2. waitAfter 12 hrs
  3. custom80% of MeOH was removed under reduced pressure
  4. customat 0° C
  5. filtrationFiltered
  6. customcrystallized solid
  7. washwashed crystals with cold diethyl ether twice

Sources & evidence

ORD record
ord-0467708ed53148819fe1e8b03061f9b5
Source dataset
uspto-grants-2011_07
Patent number
US07981904B2

Reaction notes

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