Methylamine → HCID 58954964, compound

HRID 333260Notes

Reaction equation

HRID 333260 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH:15]=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH3:19][NH2:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:19][NH:20][CH2:15][C:9]1([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:18])([F:17])[F:1])=[CH:4][CH:5]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58954873HCID 58954873, compound

Product 1

HCID 58954964HCID 58954964, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

General Procedure H2 - Reductive Amination: A mixture of 1-(4-(trifluoromethyl)phenyl)cyclohexanecarbaldehyde (256 mg, 1.0 mmol) and methylamine (2.0 M in THF, 3 ml, 6.0 mmol) in 1,2-dichloroethane was stirred at room temperature for 30 min and was then treated with sodium triacetoxyborohydride (297 mg, 1.4 mmol). The reaction mixture was stirred at room temperature overnight and was then quenched with aqueous saturated NaHCO3 solution (10 ml). The product was extracted with EtOAc (3 ×10 ml). The combined organic layers were dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography (MeOH/CH2Cl2, MeOH from 0% to 20%) to give N-methyl-1-(1-(4-(trifluoromethyl)phenyl)cyclohexyl)methanamine (178 mg, 66%). 1H NMR (CDCl3): δ 1.26-1.52 (m 4H), 1.54-1.61 (m, 2H), 1.66-1.73 (m, 2H), 2.13-2.18 (m, 2H), 2.28 (s, 3H), 2.63 (s, 2H), 7.49 (d, J=8.0 Hz, 2H), 7.59 (d, J=8.0 Hz, 2H). 13C NMR (CDCl3) δ 22.3, 26.7, 34.7, 37.5, 42.9, 64.5, 125.4, 125.9, 127.6, 128.3, 150.2.ESI MS m/z 271.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customwas then quenched with aqueous saturated NaHCO3 solution (10 ml)
  3. extractionThe product was extracted with EtOAc (3 ×10 ml)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (MeOH/CH2Cl2, MeOH from 0% to 20%)

Sources & evidence

ORD record
ord-d76e43cf5f094733b5148f414536f4bc
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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