tert-butyl 5-(5-chloro-2-ethoxyphenyl)-2H-1,4-oxazine-4(3H)-carboxylate → 3-(5-Chloro-2-ethoxyphenyl)morpholine

HRID 1615436Notes

Reaction equation

HRID 1615436 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][CH3:23])=[C:6]([C:8]2[N:9](C(OC(C)(C)C)=O)[CH2:10][CH2:11][O:12][CH:13]=2)[CH:7]=1>[Pt]=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][CH3:23])=[C:6]([CH:8]2[CH2:13][O:12][CH2:11][CH2:10][NH:9]2)[CH:7]=1

Participants

3

Reactant 1

HCID 86680672tert-butyl 5-(5-chloro-2-ethoxyphenyl)-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 866806733-(5-Chloro-2-ethoxyphenyl)morpholineYield 38%

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

This compound was prepared from tert-butyl 5-(5-chloro-2-ethoxyphenyl)-2H-1,4-oxazine-4(3H)-carboxylate using procedures similar to those described in Example 3b above. Platinum oxide was used as a catalyst. The product was isolated as a brown solid (38% yield); 1H-NMR (d6-DMSO) 1.34 (3H, s), 2.87-3.00 (3H, m), 3.42 (2H, m), 3.72-3.76 (2H, m), 4.02-4.11 (3H, m), 6.97 (1H, d), 7.25 (1H, d), 7.47 (1H, brs); 13C-NMR (d6-DMSO) 14.6, 45.9, 52.9, 63.7, 66.5, 71.1, 113.2, 126.9, 127.5; MS ES(+) 242.8 (M++1); HRMS m/z calcd for C12H16ClNO2+H+ 242.0948 [M+H+]. Found 242.0958. IR λmax=1491, 1103, 806 cm−1.

Sources & evidence

ORD record
ord-1ca8f871ddd4497a9fa7907e9bbc0224
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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