1-Pyrrolidineethanamine → HCID 9930863, compound

HRID 1356471Notes

Reaction equation

HRID 1356471 reaction equation
[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:45][CH2:46][CH2:47][N:48]1[CH2:52][CH2:51][CH2:50][CH2:49]1>C1COCC1.O.C(N(CC)CC)C.C(#N)C>[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH:45][CH2:46][CH2:47][N:48]3[CH2:52][CH2:51][CH2:50][CH2:49]3)=[O:14])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1

Participants

9

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 18508341HCID 18508341, compound

Product 1

HCID 9930863HCID 9930863, compoundYield 67.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-(4-biphenylylmethoxy)benzoic acid (1.005 g) in THF(30 ml)/acetonitrile (30 ml) were added, WSC (0.772 g), HOBt (0.516 g), 1-(2-aminoethyl)pyrrolidine (0.453 g), and triethylamine (1.2 ml). The reaction mixture was stirred at room temperature for 29 hr, diluted with water, and extracted with ethyl acetate. The organic layer was washed with 10% aqueous potassium carbonate and saturated aqueous sodium chloride sequentially, dried, and concentrated. The residue was recrystallized from ethanol/diisopropyl ether to obtain the titled compound (0.891 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 10% aqueous potassium carbonate and saturated aqueous sodium chloride sequentially
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethanol/diisopropyl ether

Sources & evidence

ORD record
ord-5b8cc9fe15ab486fbfc19228f8477902
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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