Tetrafluoro-m-phenylenediamine dihydrochloride → Tetrafluoro-m-phenylenediamine dihydrochloride

HRID 1472495Notes

Reaction equation

HRID 1472495 reaction equation
[C:1]1([NH2:12])[C:6]([F:7])=[C:5]([F:8])[C:4]([F:9])=[C:3]([NH2:10])[C:2]=1[F:11].[ClH:13].Cl.[F:15][C:16]1[CH:17]=[C:18]([N:28]2[CH2:32][CH:31]([CH2:33][NH:34]C(C3C=CC=CC=3)C)[O:30][C:29]2=[O:43])[CH:19]=[CH:20][C:21]=1[N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.FC1C=C(N2C[C@H](CN[C@H](C3C=CC=CC=3)C)OC2=O)C=CC=1N1CCOCC1>>[C:1]1([NH2:12])[C:6]([F:7])=[C:5]([F:8])[C:4]([F:9])=[C:3]([NH2:10])[C:2]=1[F:11].[ClH:13].[ClH:13].[F:15][C:16]1[CH:17]=[C:18]([N:28]2[CH2:32][C@H:31]([CH2:33][NH2:34])[O:30][C:29]2=[O:43])[CH:19]=[CH:20][C:21]=1[N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 902170523-(3-Fluoro-4-morpholinylphenyl)-5-[(1-phenylethyl)aminomethyl]-1,3-oxazolidin-2-oneHCID 902174733-(3-fluoro-4-morpholinylphenyl)-5(S)-[[(S)-1-phenylethyl]aminomethyl]-1,3-oxazolidin-2-one

Product 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 10780199(5S)-5-(Aminomethyl)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxazolidinone

Procedure

The procedure is the same as in Example 41 except that the dihydrochloride of 3-(3-fluoro-4-morpholinylphenyl)-5-[(1-phenylethyl)aminomethyl]-1,3-oxazolidin-2-one (4a) was replaced by 3-(3-fluoro-4-morpholinylphenyl)-5(S)—[[(S)-1-phenylethyl]aminomethyl]-1,3-oxazolidin-2-one ((S,S)-4b). A white solid of dihydrochloride of 3-(3-fluoro-4-morpholinylphenyl)-5(S)-aminomethyl-1,3-oxazolidin-2-one ((S)-5b) with a melting point >220° C. was obtained and at a yield of 96%; [∝]D20=−53.2° (c 0.1, H2O); 1H NMR (D2O, 400 MHz) δ: 7.48 (d, J=14.0 Hz, 1H, ArH), 7.28 (brs, 2H, ArH), 5.16-5.10 (m, IH, CH), 4.40-4.36 (m, 1H, CH2), 3.97-3.93 (m, 5H, (CH2)2O and CH2), 3.54-3.49 (m, 2H, CH2), 3.17 (brs, 4H, (CH2)2N), NH2 (hidden); TOF-MS (+Q) m/z: 296.15 (Calculated value: 296.14).

Sources & evidence

ORD record
ord-a50d220703054c10ac03a098dd3d05ba
Source dataset
uspto-grants-2015_04
Patent number
US09012631B2

Reaction notes

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