Cyclopropylamine → HCID 68673787, compound

HRID 333239Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:15]([OH:17])=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:18]1([NH2:21])[CH2:20][CH2:19]1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:15]([NH:21][CH:18]3[CH2:20][CH2:19]3)=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Reactant 2

HCID 69828Cyclopropylamine

HCID 594622HCID 594622, compound

Product 1

HCID 68673787HCID 68673787, compoundYield 25%

Procedure

The tile compound was synthesized from 1-(3,4-dichlorophenyl)-cyclohexanecarboxylic acid (372 mg, 1.37 mmol) and cyclopropylamine using General Procedure G and was isolated in 25% yield as a white solid. HPLC Rt=10.6 min; 1H NMR (400 mHz, CDCl3) 7.45 (d, J=2.2 Hz, 1H), 7.39 (d, J=8.43 Hz, 1H), 7.23-7.21 (m, 1H), 5.49 (bs, 1H), 2.62-2.59 (m, 1H), 2.25-2.20 (m, 2H), 1.84-1.78 (m, 2H), 1.59-1.55 (m, 5H), 1.38-1.33 (m, 1H), 0.73-0.68 (m, 2H), 0.37-0.33 (m, 2H); 13C NMR (100 mHz, CDCl3) 176.0, 144.8, 133.0, 131.0, 130.8, 128.6, 126.2, 50.4, 34.9, 25.7, 23.1, 6.91; GC-MS (SCOUT) 13.5 min, M+ 311.

Workup

customwas isolated in 25% yield as a white solid
customGC-MS (SCOUT) 13.5 min, M+ 311

Sources & evidence

ORD record: ord-e2fc21af353447819a4527618f7be608
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877975B2

Reaction notes

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