Morpholine → (2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(5-bromothio-phen-2-yl)-methanone

HRID 2086924Notes

Reaction equation

HRID 2086924 reaction equation
[C:1]([C:4]1[S:5][C:6](Br)=[CH:7][CH:8]=1)(=O)C.[Br:10][C:11]1[S:15][C:14]([C:16]([CH2:18][C:19]#[N:20])=[O:17])=[CH:13][CH:12]=1.C1(=O)CCCC1.N1CCOCC1.[S]>>[NH2:20][C:19]1[S:5][C:6]2[CH2:1][CH2:4][CH2:8][C:7]=2[C:18]=1[C:16]([C:14]1[S:15][C:11]([Br:10])=[CH:12][CH:13]=1)=[O:17]

Participants

6

Reactant 5

HCID 8083MorpholineHCID 8452CyclopentanoneHCID 793352-Acetyl-5-bromothiopheneHCID 5362487SulfurHCID 112876633-(5-Bromothiophen-2-yl)-3-oxopropanenitrile2×

Product 1

HCID 10268316(2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(5-bromothio-phen-2-yl)-methanoneYield 73%

Procedure

The procedure of Example 1 was followed except that 2-acetyl-5-bromothiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(5-bromothiophene-2-carbonyl)acetonitrile (Steps A and B). Cyclopentanone (Aldrich), 2-(5-bromothiophene-2-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 73%; IR (KBr) cm−1: 3349, 3236, 3130, 1590, 1549, 1431, 1414, 1269, 975; 1H NMR (CDCl3):δ2.285 (m, 2H), 2.51 (t, 2H, J=7.4 Hz), 2.70 (t, 2H, J=7.4 Hz), 6.64 (bs, 2H), 7.02 (d, 1H, J=4 Hz), 7.13 (d, 1H, J=4 Hz); red solid, mp: 154-156° C. (petroleum ether).

Sources & evidence

ORD record
ord-95733c6b68cb4bc282c79be8033c3925
Source dataset
uspto-grants-2004_04
Patent number
US06727258B2

Reaction notes

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