Benzylamine → HCID 59885594, compound

HRID 1454145Notes

Reaction equation

HRID 1454145 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-46583ae8906e4ffdacd6d18a51724665
Source dataset
uspto-grants-2009_01
Patent number
US07476680B2

Reaction notes

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