1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 9931616, compound

HRID 1356470Notes

Reaction equation

HRID 1356470 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[CH2:53][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[CH2:53][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 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 33944N-(2-Aminoethyl)piperidineHCID 757711-HydroxybenzotriazoleHCID 18508341HCID 18508341, compound

Product 1

HCID 9931616HCID 9931616, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-(4-biphenylylmethoxy)benzoic acid (1.008 g) in THF (20 ml)/acetonitrile (20 ml) were added WSC (0.775 g), HOBt (0.504 g), 1-(2-aminoethyl)piperidine (0.56 ml), and triethylamine (1.2 ml). After stirring at room temperature for 17 hr, the reaction mixture was 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 ethyl acetate/diisopropyl ether to obtain the titled compound (0.993 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 ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-a4c48158e0a14cf4a74055432a5a7b4c
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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