Triethylamine → HCID 10513201, compound

HRID 527858Notes

Reaction equation

HRID 527858 reaction equation
Br.[Br:2][CH2:3][CH2:4][CH2:5][NH2:6].C(N(CC)CC)C.[CH3:14][C:15]([CH3:20])([CH3:19])[C:16](Cl)=[O:17]>C(Cl)Cl>[Br:2][CH2:3][CH2:4][CH2:5][NH:6][C:16](=[O:17])[C:15]([CH3:20])([CH3:19])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 787013-Bromopropylamine hydrobromide

Product 1

HCID 10513201HCID 10513201, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-bromopropylamine hydrobromide (290 mg, 1.3 mmol) in CH2Cl2 (10 mL) cooled in ice bath was added triethylamine (470 uL). The resulting mixture was stirred for 5 min and trimethylacetyl chloride (163 uL, 1.3 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 2 hrs, condensed under vacuum, purified by flash chromatography to yield N-(3-bromopropyl)pivalamide as colorless oil (160 mg, 55%). 1H NMR (500 MHz, CDCl3): 8 (5.97 (br s, 1H), 3.40 (m, 4H), 2.07 (m, 2H), 1.17 (s, 9H); 13C NMR (125 MHz, CDCl3): δ 178.7, 37.2, 32.1, 31.1, 27.6.

Workup

  1. temperaturecooled in ice bath
  2. stirringThe reaction mixture was stirred at 0° C. for 2 hrs
  3. customcondensed under vacuum
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-764ff974e8b64bddbb3d337c3fa0e2a6
Source dataset
uspto-grants-2016_05
Patent number
US09346808B2

Reaction notes

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