Tert-Butyl nitrite → HCID 178462513, compound

HRID 647466Notes

Reaction equation

HRID 647466 reaction equation
[CH2:1]([N:3]1[CH2:9][CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)[CH3:2].C(O[N:16]=[O:17])(C)(C)C.[ClH:18].[NH2:19][CH2:20][C:21]#[N:22].C(N(C(C)C)C(C)C)C>C(Cl)(Cl)Cl.O1CCCC1>[ClH:18].[ClH:18].[CH2:1]([N:3]1[CH2:9][CH2:8][C:7]2=[N:19][CH:20]=[C:21]([NH2:22])[N+:16]([O-:17])=[C:6]2[CH2:5][CH2:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 10906Tert-Butyl nitriteHCID 81531DiisopropylethylamineHCID 11491918Aminoacetonitrile hydrochlorideHCID 18784290HCID 18784290, compound

Product 1

HCID 178462513HCID 178462513, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

First 23 gm (0.16 mol) of 1-ethyl-hexahydro-azepin-4-one and then 19.2 ml of tert.butylnitrite were added dropwise to a mixture of 19 gm (0.16 mol) of potassium tert.butylate and 200 ml of absolute tetrahydrofuran at -40° C., and the resulting mixture was allowed to stand overnight at 0° to 10° C. Thereafter, a solution of 20 gm (0.217 mol) of amino-acetonitrile hydrochloride and 30 gm of N-ethyl-diisopropylamine in 280 ml of chloroform was added, and the resulting mixture was refluxed for 4 hours, then filtered, and the filtrate was evaporated. The desired compound was isolated from the isomer mixture residue by silicagel chromatography with acetone/concentrated ammonia (95:5). The dihydrochloride was precipitated from ethanol with ethanolic hydrochloric acid.

Workup

  1. temperaturethe resulting mixture was refluxed for 4 hours
  2. filtrationfiltered
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-0a4d534c14b646b9a5704bb95b3c6ff5
Source dataset
uspto-grants-1983_10
Patent number
US04409220

Reaction notes

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