2-Chloro-3,6-difluorobenzoyl chloride → 2,5-Difluorobenzamide

HRID 551144Notes

Reaction equation

HRID 551144 reaction equation
[NH2:1]CC1(CC2CC2)CCN(S(NCC)(=O)=O)CC1.Cl[C:20]1[C:28]([F:29])=[CH:27][CH:26]=[C:25]([F:30])[C:21]=1[C:22](Cl)=[O:23]>>[F:29][C:28]1[CH:20]=[C:21]([C:25]([F:30])=[CH:26][CH:27]=1)[C:22]([NH2:1])=[O:23]

Participants

3

Reactant 2

HCID 27735362-Chloro-3,6-difluorobenzoyl chlorideHCID 579311884-aminomethyl-4-(cyclopropylmethyl)-N-ethylpiperidine-1-sulfonamide

Product 1

HCID 5228312,5-Difluorobenzamide

Procedure

4-Aminomethyl-4-(cyclopropylmethyl)-N-ethylpiperidine-1-sulfonamide (I-10) was treated with 2-chloro-3,6-difluorobenzoyl chloride according to the procedure outlined above to afford 2-chloro-N-{[4-cyclopropylmethyl)-1-[(ethylaminosulfonyl)]-piperidin-4-yl]methyl}-3,6-difluorobenzamide (I-12). 1H NMR (500 MHz, CD3OD): δ 7.37-7.31 (m, 1 H), 7.24-7.18 (m, 1 H), 3.53 (s, 2 H), 3.26-3.18 (m, 4 H), 3.04 (q, J=7.2 Hz, 2 H), 1.69 (t, J=5.7 Hz, 4 H), 1.37 (d, J=6.7 Hz, 2H), 1.16 (t, J=7.2 Hz, 3 H), 0.81-0.73 (m, 1 H), 0.50 (q, J=5.9 Hz, 2 H), 0.08 (q, J=4.8 Hz, 2 H); MS 450 (M+H).

Sources & evidence

ORD record
ord-51d12eb40fc147489cb104c31ca975a6
Source dataset
uspto-grants-2011_05
Patent number
US07947714B2

Reaction notes

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