Hydrochloric Acid → 3-(piperidin-4-yl)-4,5-dihydro-1H-pyrido[3,2-d][1,3]diazepin-2(3H)-one dihydrochloride

HRID 2378966Notes

Reaction equation

HRID 2378966 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[N:12][C:6]=2[CH2:5][CH2:4][N:3]1[CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1.FC(F)(F)C(O)=O.[ClH:33].C(OCC)C>ClCCl>[ClH:33].[ClH:33].[NH:16]1[CH2:17][CH2:18][CH:13]([N:3]2[CH2:4][CH2:5][C:6]3[N:12]=[CH:11][CH:10]=[CH:9][C:7]=3[NH:8][C:2]2=[O:1])[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 59006380Tert-butyl 4-(2-oxo-1,2,4,5-tetrahydropyrido[3,2-d][1,3]diazepin-3-yl)piperidine-1-carboxylate

Product 1

HCID 693141183-(piperidin-4-yl)-4,5-dihydro-1H-pyrido[3,2-d][1,3]diazepin-2(3H)-one dihydrochlorideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(2-oxo-4,5-dihydro-1H-pyrido[3,2-d][1,3]diazepin-3(2H)-yl)piperidine-1-carboxylate (0.814 g, 2.350 mmol) was dissolved in dichloromethane (8.0 ml). Trifluoroacetic acid (2.0 ml, 26.0 mmol) was added to the mixture at room temperature. The mixture was stirred at room temperature for 4 hours. All volatiles were removed and the residue was dissolved in dichloromethane (10 mL). 2M Hydrogen chloride in diethyl ether (4.11 ml, 8.22 mmol) was added to the mixture. The reaction was stirred at room temperature for 15 minutes and all volatiles were removed. The resulting off-white solid was washed 4 times with anhydrous diethyl ether. Title compound was obtained as white solid in 88% yield. 1H NMR (500 MHz, D2O) δ ppm 8.28 (d, J=4.88 Hz, 1 H) 8.05 (d, J=8.24 Hz, 1 H) 7.74-7.82 (m, 1 H) 4.30-4.41 (m, 1 H) 3.71-3.78 (m, 2 H) 3.51-3.62 (m, 2 H) 3.34-3.41 (m, 2 H) 3.09-3.20 (m, 2 H) 1.98-2.14 (m, 4 H).

Workup

  1. customAll volatiles were removed
  2. dissolutionthe residue was dissolved in dichloromethane (10 mL)
  3. stirringThe reaction was stirred at room temperature for 15 minutes
  4. customall volatiles were removed
  5. washThe resulting off-white solid was washed 4 times with anhydrous diethyl ether

Sources & evidence

ORD record
ord-97a2ff73dbe346b7be636963db47d0c7
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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