Benzo-1,3-dioxole-5-methylamine → HCID 178512308, compound

HRID 366791Notes

Reaction equation

HRID 366791 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[CH:6]([N:15]3[CH2:20][CH2:19][N:18]([C:21](SC)=[N:22][C:23]#[N:24])[CH2:17][CH2:16]3)[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3.[O:29]1[C:33]2[CH:34]=[CH:35][C:36]([CH2:38][NH2:39])=[CH:37][C:32]=2[O:31][CH2:30]1>O.C(Cl)Cl>[O:29]1[C:33]2[CH:34]=[CH:35][C:36]([CH2:38][NH:39][C:21]([N:18]3[CH2:19][CH2:20][N:15]([CH:6]4[C:7]5=[N:8][CH:9]=[CH:10][CH:11]=[C:12]5[CH2:13][S:14][C:4]5[CH:3]=[C:2]([Cl:1])[CH:28]=[CH:27][C:5]4=5)[CH2:16][CH2:17]3)=[N:22][C:23]#[N:24])=[CH:37][C:32]=2[O:31][CH2:30]1

Participants

5

Reactant 2

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 23289855HCID 23289855, compound

Product 1

HCID 178512308HCID 178512308, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 4-(8-chloro-5,11-dihydro-[1]benzothiepino[4,3-b]pyridin-11-yl)-N-cyano-1-piperazine-carboximidothioate (184 mg, 0.428 mmol) was combined with 1 ,3-benzodioxol-5-ylmethylamine [piperonylamine] (1.07 ml, 8.56 mmol) in a 10 ml flask, and the mixture was stirred at 100° C. for three hours. The reaction mixture was cooled to room temperature and diluted with water and CH2Cl2. The layers were shaken together and separated, and the aqueous extract was extracted several times with CH2Cl2. The combined organic layers were washed with brine, dried (MgSO4), filtered through `Celite` and concentrated. The residue (over 2 g) was first filtered through a plug of silica gel and eluted with 15%acetone/CH2Cl2), and then further chromatographed more carefully and eluted with 2%EtOH/CH2Cl2, increasing gradually to 40%EtOH/CH2Cl2, to afford the pure product, 155 mg (68%); MS (FAB, M+H)=533.6.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringThe layers were shaken together
  3. customseparated
  4. extractionthe aqueous extract
  5. extractionwas extracted several times with CH2Cl2
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered through `Celite` and
  9. concentrationconcentrated
  10. filtrationThe residue (over 2 g) was first filtered through a plug of silica gel
  11. washeluted with 15%acetone/CH2Cl2), and
  12. customthen further chromatographed more carefully
  13. washeluted with 2%EtOH/CH2Cl2
  14. temperatureincreasing gradually to 40%EtOH/CH2Cl2
  15. customto afford the pure product, 155 mg (68%)

Sources & evidence

ORD record
ord-6f167b55e0c748049dcb0d6e57931be8
Source dataset
uspto-grants-2000_10
Patent number
US06130229

Reaction notes

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