Dichloromethane → Isopropyl 4-(5-bromobenzo[d]oxazol-2-yl)piperidine-1-carboxylate

HRID 710078Notes

Reaction equation

HRID 710078 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:7][C:6]=2[CH:16]=1.C(Cl)Cl.C(Cl)Cl.[OH2:23]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]3[CH2:11][CH2:12][N:13]([C:8]([O:9][CH:5]([CH3:6])[CH3:4])=[O:23])[CH2:14][CH2:15]3)=[N:7][C:6]=2[CH:16]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 21908982Water methylene chlorideHCID 711141905-Bromo-2-(piperidin-4-yl)benzo[d]oxazole

Product 1

HCID 71257568Isopropyl 4-(5-bromobenzo[d]oxazol-2-yl)piperidine-1-carboxylate

Conditions

Temperature
0 °C

Procedure

Intermediate 5 (980 mg, 3.31 mmol) was dissolved in DCM (50 mol) and added TEA (0.45 ml, 3.31 mmol). Reaction mixture cooled to 0° C., isopropylchloro formate (2.7 ml, 6.62 mmol) was added and stirred the reaction mixture for 3 h at rt. Work up (DCM/H2O) followed by column purification on 60-120 mesh silica gel using EtOAc and Petether (15:85) as eluent afforded the titled compound (500 mg) as a pale-red solid.

Workup

  1. customReaction mixture
  2. customfollowed by column purification on 60-120 mesh silica gel

Sources & evidence

ORD record
ord-94829366318c41468c1072934533e56e
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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