Triethylamine → [(2-Chloroethyl)amino]-n-(4-fluoroindanyl)carboxamide

HRID 1924841Notes

Reaction equation

HRID 1924841 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[NH2:11].C(N(CC)CC)C.[Cl:19][CH2:20][CH2:21][N:22]=[C:23]=[O:24]>C(Cl)Cl>[Cl:19][CH2:20][CH2:21][NH:22][C:23]([NH:11][CH:6]1[C:7]2[C:3](=[C:2]([F:1])[CH:10]=[CH:9][CH:8]=2)[CH2:4][CH2:5]1)=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 162443184-fluoro-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 59355772[(2-Chloroethyl)amino]-n-(4-fluoroindanyl)carboxamideYield 33.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred, cold (0° C.) solution of 7.0 grams (0.046 mole) of 4-fluoroindanylamine (known compound) and 5.7 grams (0.056 mole) of triethylamine in 100 mL of methylene chloride was added 5.4 grams (0.051 mole) of 2-chloroethyl isocyanate. The cold reaction mixture was stirred for three hours at which time it was filtered. The filter cake was rinsed with methylene chloride. The filtrates were combined and concentrated under reduced pressure to a residue. The residue was triturated with hexanes and the mixture filtered. The filter cake was dried under reduced pressure to yield 4.0 grams of [(2-chloroethyl)amino]-N-(4-fluoroindanyl)carboxamide. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThe cold reaction mixture
  2. filtrationwas filtered
  3. washThe filter cake was rinsed with methylene chloride
  4. concentrationconcentrated under reduced pressure to a residue
  5. customThe residue was triturated with hexanes
  6. filtrationthe mixture filtered
  7. customThe filter cake was dried under reduced pressure

Sources & evidence

ORD record
ord-1646a22f78fb499d8946714d0c3cae23
Source dataset
uspto-grants-2012_05
Patent number
US08178567B2

Reaction notes

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