Triethylamine → 4-Nitrophenyl [4-(3,4-dichlorobenzyl)morpholin-2-yl]methylcarbamate

HRID 1371384Notes

Reaction equation

C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH:15]([CH2:19][NH2:20])[CH2:14]1.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=1)=[O:27]>ClCCl>[Cl:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH:15]([CH2:19][NH:20][C:26](=[O:27])[O:28][C:29]2[CH:30]=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=2)[CH2:14]1

Participants

Conditions

Temperature: 20 °C

Procedure

Triethylamine (0.09 ml) was added to solution of Intermediate 3 (0.150 g, 0.545 mmol) in dichloromethane (3 ml) with stirring at 20° C. under nitrogen. The solution was cooled to 0° C. and a solution of 4-nitrophenyl chloroformate (0.121 g) in dichloromethane (1 ml) was added drop-wise. The resultant mixture was stirred for 4 h at 0° C. The solution was allowed to warm to 20° C., washed with brine (4 ml), dried (MgSO4), and concentrated in vacuo. Purification by Biotage flash chromatography on silica gel, eluting with 35% ethyl acetate in cyclohexane, gave the title compound as a pale yellow solid (0.119 g). LC/MS (system A) Rt 3.01 min, Mass Spectrum m/z 441 [MH+].

Workup

temperatureThe solution was cooled to 0° C.
temperatureto warm to 20° C.
washwashed with brine (4 ml)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customPurification by Biotage flash chromatography on silica gel
washeluting with 35% ethyl acetate in cyclohexane

Sources & evidence

ORD record: ord-b26463fbee6e4ec1a3da8d4b8d5601f5
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157457B2

Reaction notes

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