Morpholine → HCID 10269549, compound
Reaction equation
C(C1C=C[S:6]C=1)(=O)C.[S:9]1[CH:13]=[CH:12][C:11]([C:14]([CH2:16][C:17]#[N:18])=[O:15])=[CH:10]1.[CH2:19]([N:26]1[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1CCOCC1.[S]>>[NH2:18][C:17]1[S:6][C:28]2[CH2:27][N:26]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:31][CH2:30][C:29]=2[C:16]=1[C:14]([C:11]1[CH:12]=[CH:13][S:9][CH:10]=1)=[O:15]Participants
6
Procedure
The procedure of Example 1 was followed except that 3-acetyl-thiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(thiophene-3-carbonyl)acetonitrile (Steps A and B). 1-Benzyl-4-piperidone (van der Klein et al., (1999) J. Med. Chem. 42: 3629-3635), 2-(thiophene-3-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 68%; IR (KBr) cm−1: 3350, 3234, 2805, 1578, 1524, 1429, 1257, 1147, 984, 856, 799, 722; 1H NMR (CDCl3):δ2.14 (m, 2H), 2.54 (t, 2H, J=5.6 Hz), 3.43 (s, 2H), 3.65 (s, 2H), 6.61 (bs, 2H), 7.33 (m, 7H), 7.58 (m, 1H); yellow solid, mp: 131-133° C. (petroleum ether).
Sources & evidence
- ORD record
- ord-06276fe17e454a63a7e02a2e7d95e1d7
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06727258B2
Reaction notes
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