Morpholine → 5-Chloro-N-(((2S,3R)-3-methylpiperidin-2-yl)methyl)benzo[d]oxazol-2-amine

HRID 60939Notes

Reaction equation

HRID 60939 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([NH:10][CH2:11][C@@H:12]3[C@H:17]([CH3:18])[CH2:16][CH2:15][CH2:14][N:13]3C(OCC=C)=O)=[N:7][C:6]=2[CH:25]=1.N1CCOCC1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([NH:10][CH2:11][C@@H:12]3[C@H:17]([CH3:18])[CH2:16][CH2:15][CH2:14][NH:13]3)=[N:7][C:6]=2[CH:25]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 117732742(2S,3R)-Allyl 2-(((5-chlorobenzo[d]oxazol-2-yl)amino)methyl)-3-methylpiperidine-1-carboxylate

Product 1

HCID 1177280155-Chloro-N-(((2S,3R)-3-methylpiperidin-2-yl)methyl)benzo[d]oxazol-2-amine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,3R)-allyl 2-(((5-chlorobenzo[d]oxazol-2-yl)amino)methyl)-3-methylpiperidine-1-carboxylate (1.18 g, 3.248 mmol) and morpholine (2.8 mL, 32.48 mmol) in THF (30 mL) was added Pd(PPh3)4 (0.375 g, 0.32 mmol). The mixture was stirred at rt for 2 h. The solvent was removed in vacuo. The crude was purified via silica gel with 0˜100% EtOAc/DCM to obtain the title compound. ESI-MS (m/z): 280 [M+1]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude was purified via silica gel with 0˜100% EtOAc/DCM

Sources & evidence

ORD record
ord-7bb8338aa3f04a7ebd52d0a2dfd01de0
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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