Hydrochloric Acid → HCID 22922287, compound

HRID 2258528Notes

Reaction equation

HRID 2258528 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][C:12]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH2:15][NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])[CH2:11][CH2:10]1)=O)(C)(C)C>CCOCC>[ClH:1].[ClH:1].[C:26]1([C:12]2([CH2:15][NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53920030HCID 53920030, compound

Product 1

HCID 22922287HCID 22922287, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dry HCl gas was passed through a solution of N-t butoxycarbonyl-4-phenyl-4-(2-methoxybenzylaminomethyl)piperidine (400 mg) in dry ether (50 ml) at 0° C. for 30 minutes. The passage of gas was stopped and the solution allowed to warm to room temperature and stirred for 2 hours. The white precipitate was filtered off and re-crystallised from ethyl acetate to afford the title compound as white needles. Mp=78°-80° C. 1H NMR (360 MHz, DMSO) δ 2.14 (2H, m, C--CH and CHH--C), 2.37 (2H, m, C--CHH and CHH--C), 2.69 (2H, s, N--CHH and CHH--N), 2.78 (2H, m, N--CHH and CHH--N), 3.19 (2H, s, CH2 --NH--CH2), 3.33 (2H, s, CH2 --NH--CH2Ar), 3.57 (3H, s, OCH3), 6.91 (1H, d, J=6.0 Hz, H-6'), 6.96 (1H, t, J=6.0 and 1.0 Hz, H-5'), 7.25 (1H, d, J=6.0 Hz, H-3'), 7.37 (1H, t, J=6.0 and 1.0 Hz, H-4'), 7.41-7.73 (5H, m, Ar H); MS (CI+) 311 (M+H+); C20H27N2O.2HCl.H2O requires C, 59.70; H, 7.77; N, 6.96. Found: C, 59.36; H, 7.95; N, 6.80%.

Workup

  1. filtrationThe white precipitate was filtered off
  2. customre-crystallised from ethyl acetate

Sources & evidence

ORD record
ord-c78ae3020fcf476da3aa74dff76a28c0
Source dataset
uspto-grants-1997_08
Patent number
US05661162

Reaction notes

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