HCID 9964644, compound → 5-{[(6-Ethyl-2-phenylpiperidin-3-yl)amino]methyl}-6-methoxy-3-methyl-1,1a,3,7b-tetrahydro-2H-cyclopropa[c]quinolin-2-one
Reaction equation
[CH2:1]([CH:3]1[NH:8][CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]([NH2:15])[CH2:5][CH2:4]1)[CH3:2].C([C@@H]1N[C@@H](C2C=CC=CC=2)[C@@H](N)CC1)C.C([C@H]1N[C@H](C2C=CC=CC=2)[C@H](N)CC1)C.[CH3:46][O:47][C:48]1[CH:57]=[C:56]2[C:51]([N:52]([CH3:60])[C:53](=[O:59])[CH:54]3[CH2:58][CH:55]32)=[CH:50][C:49]=1[CH:61]=O>>[CH2:1]([CH:3]1[NH:8][CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]([NH:15][CH2:61][C:49]2[CH:50]=[C:51]3[C:56](=[CH:57][C:48]=2[O:47][CH3:46])[CH:55]2[CH2:58][CH:54]2[C:53](=[O:59])[N:52]3[CH3:60])[CH2:5][CH2:4]1)[CH3:2]Participants
Reactant 4
Product 1
Procedure
By a procedure similar to the previous examples 9 and 9A: prepared through the reaction of 6-Ethyl-2-phenyl-piperidin-3-ylamine [or (2S,3S,6S)-6-Ethyl-2-phenyl-piperidin-3-ylamine or (2R,3R,6R)-6-Ethyl-2-phenyl-piperidin-3-ylamine] with 6-Methoxy-3-methyl-2-oxo-1a,2,3,7b-tetrahydro-1H-3-aza-cyclopropa[a]naphthalene-5-carbaldehyde [or (1S,1aR)-6-Methoxy-3-methyl-2-oxo-1a,2,3,7b-tetrahydro-1H-3-aza-cyclopropa[a]naphthalene-5-carbaldehyde or (1R,1aS)-6-Methoxy-3-methyl-2-oxo-1a,2,3,7b-tetrahydro-1H-3-aza-cyclopropa[a]naphthalene-5-carbaldehyde]. Melting Point: 231–234° C. (dec); 1H-NMR (dihydrochloride, 400 MHz, CD3OD): δ 0.48 (app. q, J=5.0 Hz, 1H), 1.02 (t, J=7.5 Hz, 3H), 1.64 (ddd, J=4.2, 9.1, 9.1 Hz, 1H), 1.70–1.85 (comp, 3H), 2.21 (ddd, J=5.0, 7.5, 9.5 Hz, 1H), 2.35–2.50 (comp, 3H), 2.61 (ddd, J=8.3, 8.3, 5.5 Hz, 1H), 3.28 (s, 3H), 3.61 (m, 1H), 3.71 (s, 3H), 4.00 (m, 1H), 4.14 (ab q, J=13.3, 6.2 Hz, 2H), 5.12 (d, J=4.97 Hz, 1H), 7.09 (d, J=12.9 Hz, 2H), 7.59–7.60 (m, 3H), 7.80–7.82 (m, 2H).
Sources & evidence
- ORD record
- ord-6893ec9e26c24cb59549bc50f20a0c24
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07119207B2
Reaction notes
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