1-Pyrrolidineethanamine → HCID 9930863, compound

HRID 1356473Notes

Reaction equation

HRID 1356473 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.C(OCC)(=O)C.C(N(CC)CC)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

8

Reactant 4

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

Product 1

HCID 9930863HCID 9930863, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-([1,1′-biphenyl]-4-ylmethoxy)benzoic acid (3 g) in THF (200 ml) were added WSC (2 g) and HOBt (1.5 g) followed by the addition of 1-(2-aminoethyl)pyrrolidine (1.1 g). After stirring at room temperature for 30 min, triethylamine (2 ml) added to the reaction mixture, which was stirred at room temperature for additional 72 hr. The reaction mixture was diluted with ethyl acetate, washed with 10% aqueous potassium carbonate and water sequentially, dried, and concentrated. The residue was recrystallized from ethanol/ethyl ether to obtain the titled compound (2.7 g).

Workup

  1. stirringwas stirred at room temperature for additional 72 hr
  2. washwashed with 10% aqueous potassium carbonate and water sequentially
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethanol/ethyl ether

Sources & evidence

ORD record
ord-efd522d5188b424f89c2f6c6e0d4a44b
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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