Ammonium Hydroxide → HCID 23289881, compound

HRID 366774Notes

Reaction equation

[Br:1][C:2]1[C:3]([Cl:28])=[CH:4][C:5]2[O:15][CH2:14][C:13]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[C:16]3[CH2:21][CH2:20][N:19](C(OCC)=O)[CH2:18][CH2:17]3)[C:6]=2[CH:27]=1.[NH4+].[OH-]>Cl>[Br:1][C:2]1[C:3]([Cl:28])=[CH:4][C:5]2[O:15][CH2:14][C:13]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[C:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[C:6]=2[CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of ethyl 4-(9-bromo-8-chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-1 1-ylidene)-1-piperidine-carboxylate (0.6 g, 1.29 mmol) in conc. HCl (5 ml) was stirred at 80° C. overnight. The reaction mixture was cooled to 0° C., basified with conc. NH4OH, and extracted with methylene chloride (2×100 ml). The organic layer was separated, washed with water (20 ml), dried (MgSO4), filtered and evaporated, yielding an oil which was chromatographed on silica gel and eluted with 10%methanol/ethylacetate containing 2% conc. NH4OH. The product, 4-(9-bromo-8-chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11-ylidene)-piperidine (470 mg., 93% yield) was obtained as a white solid, m.p. 198-199° C.; MS (CI, M+H)=391; anal.: found: C, 55.32; H, 4.15; N, 7.12; C18H16BrClN2O requires: C, 55.19; H, 4.31; N, 7.15.

Workup

extractionextracted with methylene chloride (2×100 ml)
customThe organic layer was separated
washwashed with water (20 ml)
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated
customyielding an oil which
customwas chromatographed on silica gel
washeluted with 10%methanol/ethylacetate containing 2% conc. NH4OH

Sources & evidence

ORD record: ord-a041b6ede34949fd9e1c39b36f5ede13
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130229

Reaction notes

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