Morpholine → HCID 10269507, compound

HRID 2086936Notes

Reaction equation

HRID 2086936 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]([CH: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][CH: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

Reactant 5

HCID 8083MorpholineHCID 151161-(Thiophen-3-yl)ethanoneHCID 27400753-Oxo-3-(thiophen-3-yl)propanenitrile2×HCID 5362487SulfurHCID 106552354-Benzylcyclohexanone

Product 1

HCID 10269507HCID 10269507, compoundYield 65%

Procedure

The procedure of Example 1 was followed except that 3-acetylthiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(thiophen-3-carbonyl)acetonitrile (Steps A and B). 4-Benzyl-cyclohexanone (Rosowsky et al., (1999) J. Med. Chem. 42: 1007-1017), 2-(thiophen-3-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 65%; IR (KBr) cm−1: 3401, 2920, 1560, 1547, 1419, 1260, 700; 1H NMR (CDCl3):δ0.79 (m, 1H), 1.29 (m, 2H), 1.49 (m, 1H), 2.17 (m, 3H), 2.66 (m, 2H), 7.02 (bs, 2H), 7.28 (m, 8H); mp: 57-58° C. (petroleum ether).

Sources & evidence

ORD record
ord-8fbcd6cff1f54e6690d278673417e81a
Source dataset
uspto-grants-2004_04
Patent number
US06727258B2

Reaction notes

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