Methanesulfonic Acid → (E)-3-[4-(2-Phenylethenyl)-1,2,3,6-tetrahydropyridin-1-yl]methylbenzo[b]furan methanesulfonate salt

HRID 1490040Notes

Reaction equation

HRID 1490040 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[C:6]1(/[CH:12]=[CH:13]/[C:14]2[CH2:15][CH2:16][N:17]([CH2:20][C:21]3[C:22]4[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=4[O:24][CH:25]=3)[CH2:18][CH:19]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(OCC)(=O)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[C:6]1(/[CH:12]=[CH:13]/[C:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]3[C:22]4[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=4[O:24][CH:25]=3)[CH2:16][CH:15]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 9953447(E)-3-[4-(2-phenylethenyl)-1,2,3,6-tetrahydropyridin-1-yl]methylbenzo[b]furan

Product 1

HCID 9953446(E)-3-[4-(2-Phenylethenyl)-1,2,3,6-tetrahydropyridin-1-yl]methylbenzo[b]furan methanesulfonate saltYield 78.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonic acid (0.14 ml, 2.16 mmol) was added to a solution of (E)-3-[4-(2-phenylethenyl)-1,2,3,6-tetrahydropyridin-1-yl]methylbenzo[b]furan (0.6817 g, 2.16 mmol) in ethyl acetate (15 ml) to give a white precipitate. The solid was collected under suction, washed with ethyl acetate and recrystallised from 2-propanol to afford the title compound (0.6979 g, 78%), m.p. 216.5°-218° C. (dec.); (Found: C, 67.04; H, 6.08; N, 3.44. C23H25NO4S requires C, 67.13; H, 6.13; N, 3.40%); δH (500MHz, DMSO-d6) 2.43 (3H, s, CH3SO3), 2.66 (2H, m, tetrahydropyridinyl CH2), 3.29 (1H, m, tetrahydropyridinyl CH2), 3.71 (1H, m, tetrahydropyridinyl CH2), 3.90 (2H, m, tetrahydropyridinyl CH2), 4.60 (2H, br s, ArCH2N), 5.90 (1H, s, tetrahyropyridinyl CH), 6.61 (1H, d, J 16.3Hz, CH=CHPh), 6.97 (1H, d, J 16.3Hz, CH=CHPh), 7.24 (1H, t, J 7.3Hz, ArH), 7.31-7.42 (4H, m, ArH), 7.50 (2H, d, J 7.5Hz, ArH), 7.66 (1H, d, J 7.7Hz, ArH), 7.93 (1H, d, J 7.2Hz, ArH), 8.25 (1H, s, 2-H), 10.01 (1H, br s, NH+); m/z (ES+) 316 [(M+H)+ ].

Workup

  1. customto give a white precipitate
  2. customThe solid was collected under suction
  3. washwashed with ethyl acetate
  4. customrecrystallised from 2-propanol

Sources & evidence

ORD record
ord-02c7230521d8415291474a55992f086a
Source dataset
uspto-grants-1997_10
Patent number
US05681836

Reaction notes

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