Ammonium Chloride → HCID 14601951, compound

HRID 982323Notes

Reaction equation

HRID 982323 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[Mg].[CH3:10][N:11]1[C:17]2[CH:18]=[CH:19][N:20]=[CH:21][C:16]=2[N:15]=[CH:14][C:13]2=[CH:22][CH:23]=[CH:24][N:12]12.[Cl-].[NH4+]>O1CCCC1>[CH3:10][N:11]1[C:17]2[CH:18]=[CH:19][N:20]=[CH:21][C:16]=2[NH:15][CH:14]([CH:2]2[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]2)[C:13]2=[CH:22][CH:23]=[CH:24][N:12]12

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 146019475-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine

Product 1

HCID 14601951HCID 14601951, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a warm Grignard reagent prepared from 7.2 g of 4-chloro-1-methyl piperidine and 1.4 g of magnesium metal in 50 ml of tetrahydrofuran was added a solution of 5.3 g of 5-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine in 50 ml of tetrahydrofuran. The reaction mixture was stirred at ambient temperature for 15 minutes, added to an iced ammonium chloride solution and extracted with ethyl acetate (3×). The combined organics were washed with water (2×) followed by a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated. The resultant solid was purified by means of high pressure liquid chromatography (silica gel; elution with 50% methanol/dichloromethane). Recrystallization from ethyl acetate:methanol (20:1) afforded 1.65 g of 10,11-dihydro-5-methyl-10-[(1-methyl)piperidin-4-yl]-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine, mp: 235°-238° C. (dec.).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organics were washed with water (2×)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant solid was purified by means of high pressure liquid chromatography (silica gel; elution with 50% methanol/dichloromethane)
  7. customRecrystallization from ethyl acetate:methanol (20:1)

Sources & evidence

ORD record
ord-d757679e52f1445aa511089658dd2841
Source dataset
uspto-grants-1991_02
Patent number
US04996205

Reaction notes

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