Ethyl{[4-(2-butynyloxy)phenyl]sulfonyl}acetate → Ethyl 4-([4-(2-butynyloxy)phenyl]sulfonyl)-1-(3-pyridinylmethyl)-4-piperidine carboxylate

HRID 353541Notes

Reaction equation

HRID 353541 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]#[C:18][CH3:19])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:2].Cl.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]([CH2:33][CH2:34]Cl)[CH2:30][CH2:31]Cl)[CH:23]=1>>[CH2:16]([O:15][C:12]1[CH:11]=[CH:10][C:9]([S:6]([C:5]2([C:4]([O:3][CH2:1][CH3:2])=[O:20])[CH2:34][CH2:33][N:29]([CH2:28][C:24]3[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=3)[CH2:30][CH2:31]2)(=[O:7])=[O:8])=[CH:14][CH:13]=1)[C:17]#[C:18][CH3:19]

Participants

3

Reactant 2

HCID 11335441Ethyl{[4-(2-butynyloxy)phenyl]sulfonyl}acetateHCID 698869823-Pyridyl methyl[bis(2-chloroethyl)]amine hydrochloride

Product 1

HCID 23513842Ethyl 4-([4-(2-butynyloxy)phenyl]sulfonyl)-1-(3-pyridinylmethyl)-4-piperidine carboxylateYield 5%

Procedure

Ethyl 4-{[4-(2-butynyloxy)phenyl]sulfonyl}-1-(3-pyridinylmethyl)-4-piperidine carboxylate was prepared according to the general method as outlined in example 1 (step 6), starting from (4-but-2-ynyloxy-benzenesulfonyl)-acetic acid ethyl ester (4 g, 16.9 mmol) and 3-pyridyl methyl [bis(2-chloroethyl)]amine hydrochloride (4.18 g, 18.6 mmol); 370 mg brown oil. Yield 5%; MS: 457.4 (M+H)+.

Sources & evidence

ORD record
ord-664a34b91d1f4b0582d20539012b182c
Source dataset
uspto-grants-2004_06
Patent number
US06753337B2

Reaction notes

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