Triethylamine hydrochloride → HCID 178452323, compound

HRID 1804622Notes

Reaction equation

HRID 1804622 reaction equation
[C:1]([CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#[N:2].Cl.C(N(CC)CC)C.[N-:25]=[N+:26]=[N-:27].[Na+]>C1(C)C=CC=CC=1>[NH:25]1[C:1]([CH2:3][N:4]2[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]2)=[N:2][N:27]=[N:26]1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 21936030Tert-butyl 4-(cyanomethyl)piperazine-1-carboxylate

Product 1

HCID 178452323HCID 178452323, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred suspension of 1.50 g (6.66 mmol) of the title compound from Step A above in 25 mL of anhydrous toluene was added 1.38 g (10.0 mol) of triethylamine hydrochloride followed by 0.65 g (10 mmol) of sodium azide. The resoling mixture was heated to 80° C. for 12 h then cooled to ambient temperature. All volatiles were removed in vacuo, and the residue suspended in 5 mL of brine and 1.0 N aqueous hydrogen chloride solution was added until pH of ˜4 was achieved. The aqueous phase was extracted with chloroform and the combined organics were dried over magnesium sulfate and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography eluting with a 0-100% acetone in hexanes gradient to afford the title compound (i-105) as white solid (1.1 g, 63%). 1H-NMR (500 MHz, DMSO-d6) δ 3.82 (s, 2H), 3.29 (br s, 4H), 2.38-2.34 (m, 4H), 1.36 (s, 9H). LC-MS: m/z (ES) 269.0 (MH)+.

Workup

  1. temperaturethen cooled to ambient temperature
  2. customAll volatiles were removed in vacuo
  3. addition1.0 N aqueous hydrogen chloride solution was added until pH of ˜4
  4. extractionThe aqueous phase was extracted with chloroform
  5. dry with materialthe combined organics were dried over magnesium sulfate
  6. customevaporated to dryness in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with a 0-100% acetone in hexanes gradient

Sources & evidence

ORD record
ord-a2879aad6f71419683ee5a6e0c57e492
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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