Hydrochloric Acid → HCID 131728151, compound

HRID 13004Notes

Reaction equation

HRID 13004 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]1[C:14]2[C:19]([CH:20]=[C:21]3[C:26]=1[CH:25]=[CH:24][CH:23]=[CH:22]3)=[CH:18][CH:17]=[CH:16][CH:15]=2)(C)(C)C.[ClH:28]>C(O)C>[ClH:28].[CH:25]1[C:26]2[C:21](=[CH:20][C:19]3[C:14]([C:13]=2[CH2:12][NH:11][CH2:10][CH2:9][CH2:8][NH2:7])=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11682094{3-[(Anthracen-9-ylmethyl)-amino]-propyl}-carbamic acid tert-butyl ester

Product 1

HCID 131728151HCID 131728151, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 12a (200 mg, 0.51 mmole) was dissolved in absolute ethanol (6 mL) and stirred at 0° C. for 10 minutes. A 4N HCl solution (10 mL) was added to the reaction mixture dropwise and stirred at 0° C. for 20 minutes and then at room temperature overnight. The solution was concentrated in vacuo to give 16 as a yellow solid in 90% yield. 1H NMR (CD3OD) δ 8.69 (s, 1H), 8.39 (d, 2H), 8.15 (d, 2H), 7.74 (m, 2H), 7.60 (m, 2H), 5.33 (s, 2H), 3.45 (t, 2H), 3.12 (t, 2H), 2.23 (q, 4H); 13C NMR (CD3OD): δ 6 132.6, 132.0, 131.6, 130.6, 129.0, 126.7, 124.0, 122.5, 46.6, 44.6, 38.1, 25.4. HRMS (FAB) calcd for C18H20N2.2HCl (M+H−2HCl)+ 265.1699, Found 265.1704.

Workup

  1. stirringstirred at 0° C. for 20 minutes
  2. customat room temperature
  3. customovernight
  4. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-3b2a5ed5f9f5406db02c2bbc1e859823
Source dataset
uspto-grants-2010_06
Patent number
US07728041B2

Reaction notes

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