Hydrochloric Acid → (S)-2-(9H-pyrido[2,3-b]indol-6-yl)morpholine hydrochloride

HRID 710270Notes

Reaction equation

[N:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:12][C:11]([C@@H:14]1[O:19][CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]1)=[CH:10][CH:9]=3.[ClH:27].CCOCC>O1CCOCC1>[ClH:27].[N:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:12][C:11]([C@@H:14]1[O:19][CH2:18][CH2:17][NH:16][CH2:15]1)=[CH:10][CH:9]=3

Participants

Conditions

Temperature: 60 °C

Procedure

(S)-tert-Butyl 2-(9H-pyrido[2,3-b]indol-6-yl)morpholine-4-carboxylate (22 mg, 0.062 mmol) was dissolved in dioxane (0.5 ml) and a solution of HCl in dioxane (4M, 0.19 ml, 0.75 mmol) was added. The reaction mixture was stirred for 2 h at 60° C. After cooling ether (2 ml) was added and the solid was filtered off. It was washed with ether and dried in vacuo to afford (S)-2-(9H-pyrido[2,3-b]indol-6-yl)morpholine hydrochloride (17 mg, 94%) as a light yellow solid. MS (ISP): 254.2 ([M+H]+).

Workup

additionwas added
filtrationthe solid was filtered off
washIt was washed with ether
customdried in vacuo

Sources & evidence

ORD record: ord-24a17271e0064a85b26877993db58d3a
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181230B2

Reaction notes

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