Cyclopropanemethanamine → HCID 86670990, compound

HRID 515365Notes

Reaction equation

HRID 515365 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:28])([C:24]([F:27])([F:26])[F:25])[C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1.[C:32](Cl)(=O)[O:33]C1C=CC([N+]([O-])=O)=CC=1.[CH:45]1([CH2:48][NH2:49])[CH2:47][CH2:46]1>O1CCCC1>[CH:45]1([CH2:48][NH:49][C:32]([NH:1][C:2]2[CH:31]=[CH:30][CH:29]=[C:4]([CH2:5][CH:6]3[CH2:11][CH2:10][N:9]([CH2:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([OH:28])([C:20]([F:21])([F:22])[F:23])[C:24]([F:27])([F:25])[F:26])=[CH:17][CH:18]=4)[CH2:8][CH2:7]3)[CH:3]=2)=[O:33])[CH2:47][CH2:46]1

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 821294-Nitrophenyl chloroformateHCID 86670991HCID 86670991, compound

Product 1

HCID 86670990HCID 86670990, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-((4-(3-aminobenzyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.224 mmol, 100 mg) and 4-nitrophenyl carbonochloridate (0.224 mmol, 45.1 mg) in tetrahydrofuran (5 mL) was stirred at room temperature for 30 minutes. Cyclopropylmethanamine (0.453 mmol, 46 μL, 32.2 mg) was added and the reaction was kept at room temperature overnight. The reaction mixture was concentrated under vacuum and residue purified by silica column chromatography (eluent: 2-10% methanol in dichloromethane) to afford the title compound (99 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum and residue
  2. custompurified by silica column chromatography (eluent: 2-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-bea1736103b6415f962abf9fbf500e0e
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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