Potassium Iodide → Formate

HRID 556973Notes

Reaction equation

HRID 556973 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:19])[CH2:13][CH2:12][NH:11][CH2:10][CH:9]2[NH:14][C:15](=[O:18])[CH2:16][CH3:17])=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.[I-].[K+].Br[CH2:31][CH2:32][CH:33]=[C:34]1[C:40]2[CH:41]=[CH:42][CH:43]=[N:44][C:39]=2[CH2:38][O:37][C:36]2[CH:45]=[CH:46][C:47]([C:49]([OH:52])([CH3:51])[CH3:50])=[CH:48][C:35]1=2>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([OH:19])[CH2:13][CH2:12][N:11]([CH2:31][CH2:32][CH:33]=[C:34]3[C:40]4[CH:41]=[CH:42][CH:43]=[N:44][C:39]=4[CH2:38][O:37][C:36]4[CH:45]=[CH:46][C:47]([C:49]([OH:52])([CH3:51])[CH3:50])=[CH:48][C:35]3=4)[CH2:10][CH:9]2[NH:14][C:15](=[O:18])[CH2:16][CH3:17])=[CH:6][CH:7]=1.[CH:8]([O-:19])=[O:37]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 79372,6-LutidineHCID 23136900HCID 23136900, compoundHCID 666859992-[5-(3-Bromo-propylidene)-5,1 1-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol

Product 2

HCID 283FormateYield 1,078.9%HCID 66757583HCID 66757583, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the N-[4-(4-chloro-phenyl)-4-hydroxy-piperidin-3-yl]-propionamide (0.133 g, 0.47 mmol) in isopropanol (5.0 mL) was added 2,6-lutidine (0.055 mL, 0.47 mmol) and catalytic potassium iodide. This mixture was heated to 80° C., and treated with 2-[5-(3-Bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (0.176 g, 0.35 mmol), added in portions over 2 h. The solution was then stirred at 80° C. for an additional 14 h. The reaction was concentrated in vacuo, then purified by HPLC (acetonitrile/H2O/Formic acid) to yield the title compound as a white formate salt (0.085 g, 27%). 1H-NMR (CDCl3): δ 0.780 (t, 3H), 1.55 (s, 6H), 1.90 (m, 3H), 2.60 (m, 2H), 2.92-3.28 (m, 6H), 4.50 (d, 1H), 5.26 (bs, 2H), 6.00 (t, 1H), 6.82 (d, 1H), 7.22-7.37 (m, 6H), 7.44 (s, 1H), 7.56 (d, 1H), 8.20 (d, 1H), 8.34 (s, 1H), 8.47 (d, 1H). ESI-MS m/z: 576(M+1), retention time 1.43.

Workup

  1. additionadded in portions over 2 h
  2. concentrationThe reaction was concentrated in vacuo
  3. custompurified by HPLC (acetonitrile/H2O/Formic acid)

Sources & evidence

ORD record
ord-3996eb0017184a1ab45e2c1457332450
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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