Potassium Iodide → 2-(5-{3-[6-chloro-1,2-dihydro-2-oxo-spiro[4H-3,1-benzoxazin-4,4'-piperidin]-1-yl]-propylidene}-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl)-propan-2-ol

HRID 917154Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:16][C:15](=[O:17])[O:14][C:8]3([CH2:13][CH2:12][NH:11][CH2:10][CH2:9]3)[C:6]=2[CH:7]=1.Br[CH2:19][CH2:20][CH:21]=[C:22]1[C:28]2[CH:29]=[CH:30][CH:31]=[N:32][C:27]=2[CH2:26][O:25][C:24]2[CH:33]=[CH:34][C:35]([C:37]([OH:40])([CH3:39])[CH3:38])=[CH:36][C:23]1=2.[I-].[K+]>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:16]([CH2:19][CH2:20][CH:21]=[C:22]3[C:28]4[CH:29]=[CH:30][CH:31]=[N:32][C:27]=4[CH2:26][O:25][C:24]4[CH:33]=[CH:34][C:35]([C:37]([OH:40])([CH3:39])[CH3:38])=[CH:36][C:23]3=4)[C:15](=[O:17])[O:14][C:8]3([CH2:13][CH2:12][NH:11][CH2:10][CH2:9]3)[C:6]=2[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 6-chloro-1,2-dihydro-2-oxo-spiro[4H-3,1-benzoxazin-4,4′-piperidine] (Made by the procedure of Bock, et al. GB2,355,465, 0.25 g, 0.7 mmol) in isopropanol (5 mL) was treated with 2-[5-(3-Bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (0.19 g, 0.50 mmol) and catalytic potassium iodide. The solution was stirred at 80° C. for 5 hr, and evaporated in vacuo. The residue was purified by reverse-phase preparative HPLC to yield 0.029 g (10%) of the title compound, 1H-NMR (CD3OD) δ: 1.50 (3H, s), 2.18 (2H, brs), 2.95–3.2 (6H, m), 5.30 (2H, brs), 6.18 (1H, t), 6.79(1H, m), 6.92 (1H, m), 7.12 (1H, m), 7.38 (2H, m), 7.48 (2H, m), 7.81 (2H, m), 8.31 (1H, m), 8.55 (1H, d).

Workup

customevaporated in vacuo
customThe residue was purified by reverse-phase preparative HPLC

Sources & evidence

ORD record: ord-7f5212f97ae74cb68f0d965bc412ae00
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271176B2

Reaction notes

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