Ammonia → HCID 20605024, compound

HRID 1922385Notes

Reaction equation

HRID 1922385 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:11][N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].N>ClCCCl.CO.C(Cl)Cl.C(O)(=O)C>[CH3:11][N:12]1[CH2:17][CH2:16][CH:15]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)[CH2:14][CH2:13]1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 694601,2,3,4-TetrahydroquinolineHCID 740491-Methyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 20605024HCID 20605024, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 1,2,3,4-tetrahydroquinoline (1.0 mL, 7.94 mmol) in 20 mL 1,2-dichloroethane was treated with 1-methylpiperidin-4-one (2.76 mL, 23.8 mmol) followed by sodium triacetoxyborohydride (8.4 g, 39.7 mmol) then acetic acid (2.25 mL). The suspension was stirred at room temperature for 1 day. After this time, the mixture was cooled to 0° C., quenched with 5 mL 1N NaOH and stirred for 20 minutes. The suspension was extracted with 100 mL CH2Cl2. The organic layer was dried over MgSO4, filtered and concentrated to give a light residue which was subjected to flash chromatography on silica gel using 5% MeOH/CH2Cl2 then 5% 2M NH3 in MeOH/CH2Cl2. A yellow oil was obtained (440 mg, 24.1%). 1H-NMR (CDCl3) δ: 7.07-7.02 (m, 1H), 6.95 (d, J=7.5 Hz, 1H), 6.65 (d, J=8.4 Hz, 1H), 6.55 (pseudo t, J=7.8 Hz, 1H), 3.65-3.55 (m, 1H), 3.20 (t, J=5.7 Hz, 2H), 2.99-2.95 (m, 2H), 2.73 (t, J=6.0 Hz, 2H), 2.31 (s, 3H), 2.11-2.05 (m, 2H), 1.93-1.73 (m, 6H).

Workup

  1. temperatureAfter this time, the mixture was cooled to 0° C.
  2. customquenched with 5 mL 1N NaOH
  3. stirringstirred for 20 minutes
  4. extractionThe suspension was extracted with 100 mL CH2Cl2
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a light residue which
  9. customA yellow oil was obtained (440 mg, 24.1%)

Sources & evidence

ORD record
ord-3741f36e1d8d4474932fa35188e863cd
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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