Benzylamine → HCID 59885594, compound

HRID 720893Notes

Reaction equation

HRID 720893 reaction equation
[OH:1][C@@H:2]([CH2:13][O:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]2)[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]([O-:12])=O)[CH2:6][CH2:5]1.[Li+].[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)C(C)C)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:26]([NH:33][C:10]([CH:7]1[CH2:6][CH2:5][N:4]([CH2:3][C@@H:2]([OH:1])[CH2:13][O:14][C:15]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=2[CH:17]=[CH:18][CH:19]=[N:20]3)[CH2:9][CH2:8]1)=[O:12])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 23718677HCID 23718677, compound

Product 1

HCID 59885594HCID 59885594, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Lithium (R)-1-[2-hydroxy-3-(quinolin-5-yloxy)-propyl]-piperidine-4-carboxylate (32) (100 mg; 0.297 mmol) is dissolved in methylene chloride (3 mL) at ambient temperature. Benzylamine (39) (33 mg; 0.312 mmol), N,N-diisopropylethylamine (85 mg; 0.654 mmol) and PyBOP (186 mg; 0.357 mmol) are added sequentially. The reaction is stirred for 18 hr. at room temperature, then concentrated under reduced pressure. The residue is purified via silica gel chromatography with gradient elution (90% ethyl acetate in hexanes, then 50%→100% acetone in hexanes) affording the desired product (40) as an oil. CIMS (NH3CI): 420 (MH+)

Workup

  1. concentrationat room temperature, then concentrated under reduced pressure
  2. customThe residue is purified via silica gel chromatography with gradient elution (90% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f3979263be624118a263d2b35fea3dcb
Source dataset
uspto-grants-2006_11
Patent number
US07135483B2

Reaction notes

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