Potassium Hydroxide → HCID 178477933, compound

HRID 1780795Notes

Reaction equation

HRID 1780795 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]=[C:7]2[C:12](=O)[CH:11]3[CH2:14][CH2:15][N:8]2[CH2:9][CH2:10]3)=[CH:4][CH:3]=1.[OH-].[K+].O.[NH2:21][NH2:22]>C(O)CO>[NH:8]1[CH2:15][CH2:14][CH:11]([C:12]2[CH:7]=[C:6]([C:5]3[CH:16]=[CH:17][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:22][N:21]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 2732918HCID 2732918, compound

Product 1

HCID 178477933HCID 178477933, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-(4-chlorobenzylidene)quinuclidin-3-one (35.0 g), potassium hydroxide (15.0 g) and hydrazine hydrate (11.0 cm3) in ethylene glycol(100 cm3) was heated at 110° C. for 15 minutes to produce a dear, dark brown solution. Hydrazine hydrate and water were distilled from the solution over 1 hour at 110° C. to 195° C. The brown solution was then heated at reflux for 3 hours. The mixture was cooled to room temperature and diluted with water (300 cm3). The resulting white precipitate was collected and washed with water (500 cm3) and ethyl acetate (200 cm3). The white powder was dried in vacuo to give the title compound (31.5 g, 85%), m.p. 174°-176° C.; δH (250 MHz; d6 -DMSO) 1.52 (2H, apparent qd, J=12 and 4, 2×NCH2CHAHB), 1.85 (2H, apparent d, J=10, 2×NCH2CHAHB), 2.56 (2H, apparent td, J=12 and 2, 2×NCHAHB), 2.71 [1H, tt, J=8.1 and 4.5, (CH2)2CH], 2.99 (2H, apparent d, J=12.1, 2×NCHAHB), 6.48 (1H, s, N=C--CH=C), 7.44 (2H, d, J=8.6, 2×ArH o to Cl; and 7.79 (2H, d, J=8.6, 2×ArH m to Cl); δC (90 MHz; d6 -DMSO) 39.9 (t), 34.2 (d), 46.2 (t), 98.9 (d), 126.8 (d), 128.7 (d), 131.7 (s), 132.4 (broad, s), 147.5 (broad, s) and 151.1 (broad, s); m/z (CI+, NH3) 262 (M+ +H; 60%) and 139 (100).

Workup

  1. customto produce a dear, dark brown solution
  2. distillationHydrazine hydrate and water were distilled from the solution over 1 hour at 110° C. to 195° C
  3. temperatureThe brown solution was then heated
  4. temperatureat reflux for 3 hours
  5. temperatureThe mixture was cooled to room temperature
  6. additiondiluted with water (300 cm3)
  7. customThe resulting white precipitate was collected
  8. washwashed with water (500 cm3) and ethyl acetate (200 cm3)
  9. customThe white powder was dried in vacuo

Sources & evidence

ORD record
ord-655469847fac40a7af406d5af77d87ac
Source dataset
uspto-grants-1997_05
Patent number
US05631269

Reaction notes

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