Sodium Hydroxide → HCID 9811366, compound

HRID 1978531Notes

Reaction equation

HRID 1978531 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.O.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.[OH-].[Na+]>O.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

11

Reactant 5

HCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 10943925HCID 10943925, compoundHCID 219940191-(3-Phenylpropyl)piperidin-4-amine--hydrogen chloride (1/2)

Product 1

HCID 9811366HCID 9811366, compoundYield 92.5%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (6.7 ml) was added dropwise to a suspension of 4-amino-1-(3-phenylpropyl)piperidine dihydrochloride (7.01 g) and dimethylformamide (40 ml). The mixture was stirred for 10 minutes. 5-Thia-1,8b-diazaacenaphthylene-4-carboxylic acid (5.00 g), 1-hydroxy-1H-benzotriazole monohydrate (0.710 g) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (4.61 g) were added into the reaction mixture. This was stirred for 2 hours at 68-70° C. (inner temperature). Ethyl acetate:tetrahydrofuran=4:1 (380 ml), 1N-sodium hydroxide (50 ml) and water (80 ml) were added into the reaction solution. The aqueous layer was extracted by ethyl acetate:tetrahydrofuran=4:1 (120 ml×2). The organic layer was washed with water (130 ml×3), and then concentrated. The residue which was added ethyl acetate (15 ml) was stirred for 2 hours at room temperature. The reaction mixture was dried under reduced pressure to obtain N-[1-(3-phenylpropan-1-yl)piperidin-4-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide (8.87 g, 92.5%).

Workup

  1. stirringThis was stirred for 2 hours at 68-70° C. (inner temperature)
  2. extractionThe aqueous layer was extracted by ethyl acetate
  3. washThe organic layer was washed with water (130 ml×3)
  4. concentrationconcentrated
  5. additionThe residue which was added ethyl acetate (15 ml)
  6. stirringwas stirred for 2 hours at room temperature
  7. customThe reaction mixture was dried under reduced pressure

Sources & evidence

ORD record
ord-c039023dcf0949158a64d5f5851aafdd
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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