2-Acetylthiophene → HCID 10155112, compound

HRID 2086922Notes

Reaction equation

HRID 2086922 reaction equation
[C:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)(=O)C.[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([CH2:16][C:17]#[N:18])=[O:15].[CH2:19]([N:26]1CCC(=O)CC1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1CCOCC1.[S]>>[NH2:18][C:17]1[S:5][C:4]2[CH2:1][N:26]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:6][CH2:7][C:8]=2[C:16]=1[C:14]([C:10]1[S:9][CH:13]=[CH:12][CH:11]=1)=[O:15]

Participants

6

Reactant 5

HCID 69202-AcetylthiopheneHCID 8083MorpholineHCID 192201-Benzyl-4-piperidoneHCID 1418532-Thenoylacetonitrile2×HCID 5362487Sulfur

Product 1

HCID 10155112HCID 10155112, compoundYield 78%

Procedure

The procedure of Example 1 was followed except that 2-acetylthiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(thiophene-2-carbonyl)acetonitrile (Steps A and B). 1-Benzyl-4-piperidone (van der Klein et al., (1999), J. Med. Chem. 42: 3629-3635), 2-(thiophene-2-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 78%; IR (KBr) cm−1: 3412, 2928, 1570, 1419, 1355, 1265, 1119, 700; 1H NMR (CDCl3):δ2.35 (t, 2H, J=5.2 Hz), 2.59 (t, 2H, J=5.6 Hz), 3.47 (s, 2H), 3.67 (s, 2H), 6.26 (bs, 2H), 7.05 (m, 1H), 7.30 (d, 1H, J=5.2 Hz), 7.35 (m, 5H), 7.53 (d, 1H, J=4 Hz); yellow solid, mp: 122-123° C. (petroleum ether).

Sources & evidence

ORD record
ord-58b3497383784816b00a06797cd87331
Source dataset
uspto-grants-2004_04
Patent number
US06727258B2

Reaction notes

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