Morpholine → HCID 69303148, compound

HRID 1266023Notes

Reaction equation

HRID 1266023 reaction equation
N1(C2C=CC(C3N4CCC5NC(=O)C=CC(C=54)=CN=3)=C(C)C=2)CCOCC1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.[O:34]=[C:35]1[NH:44][C:43]2[CH2:42][CH2:41][N:40]3[C:45]([C:48]4[CH:55]=[CH:54][C:51]([CH:52]=O)=[CH:50][CH:49]=4)=[N:46][CH:47]=[C:38]([C:39]=23)[CH:37]=[CH:36]1.[K+].[Br-]>CO.C(Cl)(Cl)Cl>[N:28]1([CH2:52][C:51]2[CH:54]=[CH:55][C:48]([C:45]3[N:40]4[CH2:41][CH2:42][C:43]5[NH:44][C:35](=[O:34])[CH:36]=[CH:37][C:38]([C:39]=54)=[CH:47][N:46]=3)=[CH:49][CH:50]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 253877Potassium BromideHCID 86758918HCID 86758918, compoundHCID 178519438HCID 178519438, compound

Product 1

HCID 69303148HCID 69303148, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Using the reductive amination procedure described in Example 32, 0.097 g (38%) of 1-(4-morpholin-4-yl methyl-phenyl)-8,9-dihydro-7H-2,7,9a-triaza-benzo[cd]azulen-6-one was prepared from morpholine and 4-(6-oxo-6,7,8,9-tetrahydro-2,7,9a-triaza-benzo[cd]azulen-1-yl)-benzaldehyde as a white solid: mp=285-286° C. (dec); Rf=0.11 (5% MeOH/CHCl3); IR (KBr) 1661, 1653, 1483, 1113 cm−1; 1H NMR (DMSO-d6) δ 2.40-2.41 (m, 4H), 3.15-3.17 (m, 2H), 3.26-3.61 (m, 6H), 4.45-4.46 (m, 2H), 7.35 (t, 1H, J=7.8 Hz), 7.51 (d, 2H, J=8.1 Hz), 7.82 (d, 2H, J=8.1 Hz), 7.84-7.90 (m, 2H), 8.43-8.47 (m, 1H). HRMS calcd for C21H22N4O2 362.1743 (M+), found 362.1737. Anal. (C21H22N4O2) C, H, N.

Sources & evidence

ORD record
ord-04778ccfd6b747f899199cae85cc7c0b
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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