2-Chloro-N,N-dimethylethylamine → HCID 86735519, compound

HRID 1678948Notes

Reaction equation

HRID 1678948 reaction equation
[CH2:1]([O:8][C:9](NCCCCCC(O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([N:22]([CH2:25]C)[CH2:23][CH3:24])C.C[N:28](C)[CH2:29][CH2:30]Cl>C(OCC)(=O)C>[CH3:25][N:22]([CH3:20])[CH2:23][CH2:24][O:10][C:9](=[O:8])[CH:29]([NH2:28])[CH2:30][CH2:1][CH2:2][CH2:3][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 8471TriethylamineHCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acid

Product 1

HCID 86735519HCID 86735519, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-benzyloxycarbonyl-6-aminocaproic acid, (2.65 g, 0.010 mole) in ethyl acetate (60 ml) was treated with triethylamine (2.8 ml, 0.020 mole) and 1.48M β-dimethylaminoethyl chloride (17 ml, 0.025 mole) and refluxed for 16 hrs. The reaction mixture was filtered and the filtrate extracted with saturated NaCl (3 × 50 ml), 5% NaHCO3 (3 × 50 ml), saturated NaCl (3 × 50 ml), dried over MgSO4, filtered and evaporated to dryness. The product was obtained as a viscous oil, 1.55 g (46.1%).

Workup

  1. temperaturerefluxed for 16 hrs
  2. filtrationThe reaction mixture was filtered
  3. extractionthe filtrate extracted with saturated NaCl (3 × 50 ml), 5% NaHCO3 (3 × 50 ml), saturated NaCl (3 × 50 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe product was obtained as a viscous oil, 1.55 g (46.1%)

Sources & evidence

ORD record
ord-71eeec8411134e219c5bfe6c9dd700bb
Source dataset
uspto-grants-1978_03
Patent number
US04078049

Reaction notes

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