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Hydrochloric Acid → Hydrochloric Acid

HRID 353260
Notes
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Reaction equation

HRID 353260 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[N+:16]([C:19]1[CH:24]=[C:23]([Cl:25])[C:22](Cl)=[CH:21][C:20]=1[CH2:27][C:28]([N:30]([CH3:49])[C@@H:31]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([N+:41]([O-:43])=[O:42])[CH:39]=2)CC[C@H:32]1[N:44]1[CH2:48][CH2:47][CH2:46][CH2:45]1)=[O:29])([O-:18])=[O:17].[N+](C1C=CC=CC=1CC(O)=O)([O-])=O.N1C=CC=CC=1.Cl.O(CC)CC.Cl>>[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:27][C:28]([N:30]([CH3:49])[C@@H:31]([C:40]1[CH:35]=[CH:36][CH:37]=[C:38]([N+:41]([O-:43])=[O:42])[CH:39]=1)[CH2:32][N:44]1[CH2:45][CH2:46][CH2:47][CH2:48]1)=[O:29])([O-:18])=[O:17].[ClH:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10868Dicyclohexylcarbodiimide2×HCID 77337(2-Nitrophenyl)acetic acidHCID 10953452Ether hydrochlorideHCID 228794362-(2-Nitro-4,5-dichlorophenyl)-N-methyl-N-[(+/-)-trans-2-(1-pyrrolidinyl)-7-nitro-1,2,3,4-tetrahydronaphth-1-yl]acetamide

Product 2

HCID 313Hydrochloric AcidHCID 117742682-(2-Nitrophenyl)-N-methyl-N-[(1S)-1-(3-nitrophenyl)-2-(1-pyrrolidinyl)ethyl]acetamide

Procedure

This compound was prepared via the general DCC/pyr coupling procedure from 8 (1.4886 g, 5.97 mmol), 2-nitrophenylacetic acid (2.1619 g, 11.93 mmol), DCC(2.5402 g, 12.31 mmol), and pyridine (1.00 mL, 12.36 mmol). The crude product was converted to the HCl salt with Et2O—HCl without chromatography and crystallized from MeOH—Et2O. The first crop was recrystallized again from MeOH—Et2O to yield 10 HCl.(1.3663 g, 51%): m.p. (HCl salt) 258-259° C.; 1H NMR (HCl salt, DMSO-d6) δ1.97 (br s, 4H, —CH2CH2—), 2.91 (s, 3H, —NCH3), 3.11-4.45 (complex, 8H, 4 —CH2—), 6.17 (m, 1H, —CH—), 7.51-8.25 (complex, 8H, aromatic). MS(FAB) m/z 413. Anal. (C, H, N) C21H24N4O5.HCl.0.25H2O.

Workup

  1. customcrystallized from MeOH—Et2O
  2. customThe first crop was recrystallized again from MeOH—Et2O

Sources & evidence

ORD record
ord-6d1e04bfdd0346869742df3d1ebce36e
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06750216B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes