Methanol → HCID 59295918, compound

HRID 2233413Notes

Reaction equation

HRID 2233413 reaction equation
[C:1]1([CH3:10])[C:2]([N:7]=[C:8]=[O:9])=[CH:3][CH:4]=[CH:5][CH:6]=1.[NH2:11][CH2:12][C@@H:13]([OH:30])[CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[CH2:17][CH2:16]1.CO>ClCCl>[Cl:29][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[Cl:28])[O:21][CH:18]1[CH2:17][CH2:16][N:15]([CH2:14][C@H:13]([OH:30])[CH2:12][NH:11][C:8]([NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:10])=[O:9])[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 887MethanolHCID 691942-Tolyl isocyanateHCID 11151315(2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl)propan-2-ol

Product 1

HCID 59295918HCID 59295918, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of o-tolylisocyanate (64 ml, 0.51 mmol) in dichloromethane (1 ml) was added to a suspension of (2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propan-2-ol (0.15 g, 0.47 mmol) in dichloromethane (3 ml) over a five minute period. After 1 h methanol (1 ml) was added and the solvents removed under vacuum. The residue was purified by reverse phase chromatography (C8 Symmetry column) to give the title compound (87 mg).

Workup

  1. customthe solvents removed under vacuum
  2. customThe residue was purified by reverse phase chromatography (C8 Symmetry column)

Sources & evidence

ORD record
ord-54dd8622dacd42cebd961a8c7d594fd7
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

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