Methylamine → HCID 68673625, compound

HRID 333241Notes

Reaction equation

HRID 333241 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH:14]=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.CN.[C:18]([BH3-])#[N:19].[Na+].C(OC(OCC)OCC)C.C([O-])([O-])=O.[K+].[K+]>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:14][NH:19][CH3:18])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 31214Ethyl orthoformateHCID 5003444Sodium cyanoborohydrideHCID 82127956HCID 82127956, compound

Product 1

HCID 68673625HCID 68673625, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(3-chlorophenyl)cyclohexane-carbaldehyde (119 mg, 0.53 mmol), methyl amine (291 μL, 0.58 mmol, 2.0 M in THF) and sodium cyanoborohydride (100 mg, 1.59 mmol) in 1:1 MeOH:Triethylorthoformate (4 mL) was shaken at RT overnight. The solution was poured into saturated aqueous K2CO3 and washed with EtOAc (2×20 mL). The combined organic washes were dried (Na2SO4), filtered and concentrated. The crude material was dissolved in Et2O and HCl (1.5 mL, 2.0 M in Et2O) was added. The reaction was concentrated and the HCl salt was recrystallized from CH3CN (4.5 mL) to give pure (1-(3-chlorophenyl)cyclohexyl)-N-methylmethanamine hydrochloride as colorless crystals HPLC Rt=8.25 min; 1H NMR (400 mHz, MeOH-d4) 7.43-7.28 (m, 4H) 3.12 (s, 2H), 2.54 (s, 3H), 2.19-2.16 (m, 2H), 1.67-1.30 (m, 8H); LC-MS 7.29 min, (M+1)− 238 @ 7.50 min.

Workup

  1. washwashed with EtOAc (2×20 mL)
  2. dry with materialThe combined organic washes were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe crude material was dissolved in Et2O
  6. additionHCl (1.5 mL, 2.0 M in Et2O) was added
  7. concentrationThe reaction was concentrated
  8. customthe HCl salt was recrystallized from CH3CN (4.5 mL)

Sources & evidence

ORD record
ord-1059f16ea6d9413d8ff2be5730922090
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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