Dimethylamine → HCID 58993667, compound

HRID 391437Notes

Reaction equation

HRID 391437 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH2:11][O:12][CH2:13][C:14]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:10]=1)[C:5](O)=[O:6].[CH3:33][NH:34][CH3:35].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>CN(C)C=O.C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([C:5](=[O:6])[N:34]([CH3:35])[CH3:33])[CH:3]=1)[CH2:11][O:12][CH2:13][C:14]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 58993646HCID 58993646, compound

Product 1

HCID 58993667HCID 58993667, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 3-bromo-5-(((1-(tert-butoxycarbonyl)-4-phenylpiperidin-4-yl)methoxy)methyl)benzoic acid (160 mg, 0.32 mmol) in dimethylformamide (5 mL) was cooled to 0° C. and sequentially treated with methylene chloride (2 mL), dimethylamine (1 N in tetrahydrofuran, 0.32 mL, 0.32 mmol), N,N-diisopropylethylamine (90 μL, 0.64 mmol), and PyBop® (0.21 g, 0.38 mmol). The solution was stirred for 1.5 h and concentrated. The product was purified by column chromatography (30% ethyl acetate/hexanes) to give 120 mg (70%). 1H-NMR (CDCl3, 500 MHz) δ 7.38-7.40 (m, 1H), 7.33-7.35 (m, 4H), 7.22-7.24 (m, 2H), 7.03 (s, 1H), 4.32 (s, 2H), 3.74-3.77 (m, 2H), 3.38 (s, 2H), 3.08 (s, 3H), 2.99-3.05 (m, 2H), 2.90 (s, 3H), 2.16-2.19 (m, 2H), 1.83-1.89 (m, 2H), 1.43 (s, 9H). Mass spec.: 533.24 (MH)+.

Workup

  1. concentrationconcentrated
  2. customThe product was purified by column chromatography (30% ethyl acetate/hexanes)
  3. customto give 120 mg (70%)

Sources & evidence

ORD record
ord-7a883e10fa34466c9e2ecc8f7a4ea52a
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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