4-(Aminomethyl)cyclohexanecarboxylic acid → 4-((N-(4-fluorobenzyl)-4-methylphenylsulfonamido)methyl)-cyclohexanecarboxylic acid

HRID 658618Notes

Reaction equation

HRID 658618 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.[NH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]1.[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>>[F:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:10]([CH2:11][CH:12]2[CH2:13][CH2:14][CH:15]([C:18]([OH:20])=[O:19])[CH2:16][CH2:17]2)[S:28]([C:25]2[CH:26]=[CH:27][C:22]([CH3:21])=[CH:23][CH:24]=2)(=[O:30])=[O:29])=[CH:4][CH:5]=1

Participants

4

Reactant 3

HCID 55264-(Aminomethyl)cyclohexanecarboxylic acidHCID 73974-Toluenesulfonyl chlorideHCID 680214-Fluorobenzyl bromide

Product 1

HCID 238528344-((N-(4-fluorobenzyl)-4-methylphenylsulfonamido)methyl)-cyclohexanecarboxylic acid

Procedure

Prepared as in example 5-11 from 1-(bromomethyl)-4-fluorobenzene, 4-(aminomethyl)cyclohexanecarboxylic acid and 4-methylbenzene-1-sulfonylchloride. MS (M+H, 420); 1H NMR (400 MHz, DMSO-d6): δ, ppm: 0.71 (m, 2H)), 0.95 (m, 2H), 1.15 (br, s, 1H), 1.51 (d, 2H), 1.76 (d, 2H), 2.0 (1H), 2.40 (s, 3H), 2.85 (m, 2H), 4.22 (s, 2H), 7.14 (m, 2H), 7.32 (m, 2H), 7.40 (m, 2H), 7.69 (m, 2H), 11.93 (br, s, 1H).

Sources & evidence

ORD record
ord-e3d2ab12cfcf4ef588cfcb5e16659835
Source dataset
uspto-grants-2011_12
Patent number
US08076491B2

Reaction notes

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