Triethylamine → HCID 22914785, compound

HRID 1377575Notes

Reaction equation

HRID 1377575 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][N:19]([C:22](=[O:24])C)[CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:25]=1.[CH2:26]([N:28](CC)CC)C.CN=C=O>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][N:19]([C:22]([NH:28][CH3:26])=[O:24])[CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:25]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 60680Sch 37370

Product 1

HCID 22914785HCID 22914785, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2.03 g (6.53 mmole) of 8-chloro-11-(1-acetyl-4-piperidylidene)-6,11-dihydro-5 H-benzo[5,6]cyclohepta[1,2-b]pyridine and 1.0 mL of triethylamine in 30 mL of dry THF at -10° C. and under a nitrogen atmosphere was added dropwise over 10 minutes 0.40 mL (6.78 mmole) of methylisocyanate. The mixture was slowly warmed to room temperature. After 4 hours it was poured in water and extracted 3× with CH2Cl2. The organic portions were combined, dried over MgSO4, filtered and concentrated in vacuo to afford a product which was recrystallized from CH2Cl2 ethyl acetateexanes to give 1.70 g of the title compound as white crystals. (m.p. 194.5°-196° C.).

Workup

  1. extractionextracted 3× with CH2Cl2
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto afford a product which
  6. customwas recrystallized from CH2Cl2 ethyl acetateexanes

Sources & evidence

ORD record
ord-295b0108988341468b17b61902767392
Source dataset
uspto-grants-1997_09
Patent number
US05665726

Reaction notes

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