Dimethylamine → 1-(4-ethynylphenyl)-N,N-dimethylmethanamine

HRID 1466302Notes

Reaction equation

HRID 1466302 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[CH:2].[CH3:11][NH:12][CH3:13].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(O)(=O)C.ClCCCl>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:12]([CH3:13])[CH3:11])=[CH:5][CH:4]=1)#[CH:2]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 27716454-EthynylbenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 866588291-(4-ethynylphenyl)-N,N-dimethylmethanamineYield 92%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

Glacial acetic acid (3 drops) was added to a mixture of 4-ethynylbenzaldehyde (250.7 mg, 1.93 mmol), dimethylamine (2M in THF, 1.5 mL, 3.0 mmol) and NaBH(OAc)3 (617 mg, 2.91 mmol) in DCE (6.5 mL). The resulting mixture was stirred for 2.5 h at rt. The reaction was quenched with saturated aqueous NaHCO3 (˜40 mL). The product was extracted into CH2Cl2 (100 mL, then 2×50 mL), and the combined organic layer was washed with brine (25 mL), dried (Na2SO4) and evaporated in vacuo. Purification on Biotage Isolera (silica, 0-3% 2M NH3-methanol/CH2Cl2) gave 1-(4-ethynylphenyl)-N,N-dimethylmethanamine (280.1 mg, 92%). 1H NMR (400 MHz, CDCl3) δ 7.46 (d, J=8 Hz, 2H), 7.28 (d, J=8 Hz, 2H), 3.42 (s, 2H), 3.07 (s, 1H), 2.24 (s, 6H).

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3 (˜40 mL)
  2. extractionThe product was extracted into CH2Cl2 (100 mL
  3. wash2×50 mL), and the combined organic layer was washed with brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customPurification on Biotage Isolera (silica, 0-3% 2M NH3-methanol/CH2Cl2)

Sources & evidence

ORD record
ord-cd049711b2b5479e9166996e0b0265ed
Source dataset
uspto-grants-2015_04
Patent number
US08999968B2

Reaction notes

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