Hydrochloric Acid → HCID 67751501, compound

HRID 2210703Notes

Reaction equation

HRID 2210703 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH:9]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)(C)(C)C.[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([Cl:30])[CH:29]=1)[CH2:25]Br.Cl>>[ClH:21].[Cl:21][C:22]1[CH:23]=[C:24]([CH2:25][O:14][C@H:10]2[CH2:11][CH2:12][CH2:13][NH:8][C@H:9]2[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:27]=[C:28]([Cl:30])[CH:29]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 125839781-(Bromomethyl)-3,5-dichlorobenzeneHCID 215840931-t-Butyloxycarbonyl-3-hydroxy-2-phenylpiperidine

Product 1

HCID 67751501HCID 67751501, compound

Procedure

The title compound was prepared from 1-t-butyloxycarbonyl-3-hydroxy-2-phenylpiperidine (Example 2c) and 3,5-dichlorobenzylbromide in an analogous manner to that described in Example 2d, e, m.p.=243°-245° C. 1H NMR (360 MHz, CDCl3) 1.49-1.53 (1H, m, CHH), 1.60-1.70 (1H, m, CHH), 1.82-1.95 (1H, m, CHH), 2.14-2.18 (1H, m, CHH), 2.79-2.87 (1H, m, NCHH), 3.27-3.31 (1H, m, NCHH), 3.60 (1H, s, OCHCHN), 3.82 (1H, s, OCHCHN), 4.02-4.05 (1H, d, J=13 Hz, OCHH), 4.31-4.35 (1H, d, J=13 Hz, OCHH), 6.80 (2H, s, ArH), 7.15 (1H, s, ArH), 7.25-7.35 (5H, m, ArH). Found: C, 58.24; H, 5.38; N, 3.91. Calcd. for C18H19NOCl2.HCl C, 58.01; H, 5.41; N, 3.76%.

Sources & evidence

ORD record
ord-d0e8840df23d4677a9418392176b7c71
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

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