Sodium Hydroxide → HCID 9811366, compound

HRID 1978532Notes

Reaction equation

HRID 1978532 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6][CH2:5]1.[N:19]1[CH:20]=[C:21]2[N:30]3[C:25](=[CH:26][CH:27]=[CH:28][C:29]=13)[S:24][C:23]([C:31](O)=[O:32])=[CH:22]2.C(P(=O)(OCC)OCC)#N.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C.CN(C)C=O.C(N(CC)CC)C>[C:13]1([CH2:12][CH2:11][CH2:10][N:7]2[CH2:8][CH2:9][CH:4]([NH:3][C:31]([C:23]3[S:24][C:25]4[N:30]5[C:21](=[CH:20][N:19]=[C:29]5[CH:28]=[CH:27][CH:26]=4)[CH:22]=3)=[O:32])[CH2:5][CH2:6]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 76257Diethyl cyanophosphonateHCID 10943925HCID 10943925, compoundHCID 219940191-(3-Phenylpropyl)piperidin-4-amine--hydrogen chloride (1/2)

Product 1

HCID 9811366HCID 9811366, compoundYield 63.6%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (1.34 ml) was added dropwise to a suspension of 4-amino-1-(3-phenylpropyl)piperidine dihydrochloride (1.40 g) and dimethylformamide (10 ml). Into the mixture which was stirred for 10 minutes, 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid (1.00 g) and diethyl cyanophosphonate (0.81 ml) were added. The mixture was stirred for 1 hour at room temperature, and 2 hours at 55° C. Ethyl acetate:tetrahydrofuran=4:1 (1.75 ml) and 1N-sodium hydroxide (30 ml) were added into the reaction mixture. The organic layer which was washed with sodium hydroxide (30 ml×3) and water (30 ml×2) was concentrated. The residual crystal which was added acetate (4 ml) was stirred for 1 hour at room temperature. This was dried under reduced pressure to obtain N-[1-(3-phenylpropan-1-yl)piperidin-4-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide (1.07 g, 63.6%).

Workup

  1. stirringThe mixture was stirred for 1 hour at room temperature
  2. custom2 hours
  3. customat 55° C
  4. washThe organic layer which was washed with sodium hydroxide (30 ml×3) and water (30 ml×2)
  5. concentrationwas concentrated
  6. additionThe residual crystal which was added acetate (4 ml)
  7. stirringwas stirred for 1 hour at room temperature
  8. customThis was dried under reduced pressure

Sources & evidence

ORD record
ord-e4877aefddcc424f842d07ea5ef470e9
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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