Ammonium Chloride → 10-[(2-Bromo-5-pyridinyl)methyl]-8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine

HRID 37360Notes

Reaction equation

[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[O:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][NH:10][C:4]=2[CH:3]=1.C([Li])CCC.Cl[CH2:23][C:24]1[CH:25]=[N:26][C:27]([Br:30])=[CH:28][CH:29]=1.[NH4+].[Cl-]>C1COCC1.CCCCCC>[Br:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][N:10]2[CH2:9][C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[O:6][C:5]3[CH:15]=[CH:16][C:2]([Cl:1])=[CH:3][C:4]2=3)=[CH:25][N:26]=1

Participants

Conditions

Temperature: -23 °C

Procedure

To a stirred solution of 8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine (2 g) in THF (25 mL) at -78° C. was added 1.6 M hexane solution of n-butyl lithium (5.4 mL). After 25 minutes, 3-chloromethyl-6-bromopyridine (1.79 g) in THF (5 mL) was added. After 30 minutes, the temperature was raised to -23° C. After 30 minutes, an excess saturated solution of NH4Cl was added and the mixture was extracted with ether. The organic extract was dried over MgSO4 and concentrated. The residue was chromatographed over silica gel using 10% ethyl acetate in hexane as eluant. Appropriate fractions were pooled to give the title compound (2.8 g) as a thick gum.

Workup

waitAfter 30 minutes
waitAfter 30 minutes
extractionthe mixture was extracted with ether
extractionThe organic extract
dry with materialwas dried over MgSO4
concentrationconcentrated
customThe residue was chromatographed over silica gel using 10% ethyl acetate in hexane as eluant

Sources & evidence

ORD record: ord-9ffddc0596474edc81dec07df29cf66a
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420270

Reaction notes

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