Water → HCID 178420598, compound

HRID 1061220Notes

Reaction equation

C(=O)C1C=CC=CC=1.[O:9]1[C:13]2([CH2:18][CH2:17][N:16]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[O:12][CH2:11][CH2:10]1.[N-:27]=[N+:28]=[N-:29].[Na+].Cl.C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[NH:27]1[C:23]([C:22]2[CH:25]=[CH:26][C:19]([N:16]3[CH2:17][CH2:18][C:13]4([O:12][CH2:11][CH2:10][O:9]4)[CH2:14][CH2:15]3)=[CH:20][CH:21]=2)=[N:24][N:29]=[N:28]1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 4-(1,4-dioxa-8-azaspiro(4.5)dec-8-yl)benzonitrile benzaldehyde (Taylor, E. C., Skotnicki, J. S. Synthesis, 1981, 606) (10 mmol, 2.44 g), sodium azide (30 mmol, 1.95 g) and triethylamine hydrochloride (30 mmol, 4.13 g) in toluene was heated to ˜95° C. over night (Koguro, K., Oga, T., Missui, S. and Orita, R. Synthesis, 1998, 910). After cooling the mixture was poured into water and the solid which was formed was collected. To the aqueous layer 36% hydrochloric acid was added dropwise to salt out more solid. The combined solids were dried to yield the title compound as an off-white solid (2.30 g, 80%); 1H NMR (300 MHz, DMSO-d6) δ 1.70 (t, J=5.7 Hz, 4H), 3.44 (t, J=5.7 Hz, 4H), 3.92 (s, 4H), 7.12 (d, J=9.0 Hz, 2H), 7.85 (d, J=9.0 Hz, 2H); MS (ES) m/z: 288.4 (MH+); HRMS Calcd. for C14H17N5O (M+): 287.1382. Found: 287.1375.

Workup

custom(Koguro, K., Oga, T., Missui, S. and Orita, R. Synthesis, 1998, 910)
temperatureAfter cooling the mixture
customthe solid which was formed
customwas collected
additionTo the aqueous layer 36% hydrochloric acid was added dropwise to salt out more solid
customThe combined solids were dried

Sources & evidence

ORD record: ord-9f767dadbb3a4620b775f3841ac1ce1a
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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