Acetic Acid → HCID 28978254, compound

HRID 1922387Notes

Reaction equation

HRID 1922387 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:9][N:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH:13]1[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 119952-IodoanilineHCID 740491-Methyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 28978254HCID 28978254, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2-iodoaniline (1.0 g, 4.57 mmol) in 15 mL 1,2-dichloroethane was treated with 1-methylpiperidin-4-one (530 μL, 4.57 mmol) followed by sodium triacetoxyborohydride (1.55 g, 7.31 mmol) then acetic acid (259 μL). The suspension was stirred at room temperature for 21 hours. After this time, the mixture was cooled to 0° C., quenched with 20 mL 1N NaOH and extracted with 2×100 mL CH2Cl2. The combined organic layer was dried over MgSO4, filtered and concentrated. The residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2. A light yellow oil was obtained (579 mg, 40.2%). 1H-NMR (CDCl3) δ 7.64 (dd, J=1.2, 8.1 Hz, 1H), 7.21-7.15 (m, 1H), 6.57 (d, J=8.1 Hz, 1H), 6.44-6.39 (m, 1H), 4.12-4.10 (m, 1H), 3.37-3.35 (m, 1H), 3.79-2.75 (m, 2H), 2.31 (s, 3H), 2.22-2.03 (m, 4H), 1.65-1.53 (m, 2H). MS (ESI): 317.1 (M+1, 100%).

Workup

  1. temperatureAfter this time, the mixture was cooled to 0° C.
  2. customquenched with 20 mL 1N NaOH
  3. extractionextracted with 2×100 mL CH2Cl2
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customA light yellow oil was obtained (579 mg, 40.2%)

Sources & evidence

ORD record
ord-ed95ce06f5d54d8fb94838b247136110
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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