Ammonia → N,N-Dimethyl-3,4-dioleyloxybenzylamine

HRID 1988506Notes

Reaction equation

HRID 1988506 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[CH2:5]([O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:42]\[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH:27]=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[BH4-].[Na+].N>C(O)C.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[CH3:2][N:3]([CH2:27][C:26]1[CH:29]=[CH:30][C:31]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:42]\[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[C:24]([O:23][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:25]=1)[CH3:4]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 10473Dimethylamine, hydrochlorideHCID 4311764Sodium borohydrideHCID 161030163,4-Dioleyloxybenzaldehyde

Product 1

HCID 23642188N,N-Dimethyl-3,4-dioleyloxybenzylamine

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of triethylamineamine (2.0 mL, 14 mmol) in ethanol (20 mL) was added dimethylamine hydrochloride (1.63 g, 20 mmol), titanium tetraisopropoxide (5.96 mL, 20 mmol) and 3,4-dioleyloxybenzaldehyde (6.39 g, 10 mmol). The mixture was allowed to stir under argon for 10 h at room temperature. Sodium borohydride (0.57 g, 15 mmol) was added to the reaction mixture which was then allowed to stir at room temperature overnight. Concentrated aqueous ammonia (4 mL) was added slowly to the reaction mixture. The reaction mixture was filtered and the solids washed with dichloromethane. The filtrate was dried over K2CO3, filtered and concentrated. The resultant oil was purified via flash chromatography (2-10% acetone in dichloromethane, 0.5% TEA gradient) to afford 5.81 g (87-+%) of a yellow oil.

Workup

  1. stirringto stir at room temperature overnight
  2. filtrationThe reaction mixture was filtered
  3. washthe solids washed with dichloromethane
  4. dry with materialThe filtrate was dried over K2CO3
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant oil was purified via flash chromatography (2-10% acetone in dichloromethane, 0.5% TEA gradient)
  8. customto afford 5.81 g (87-+%) of a yellow oil

Sources & evidence

ORD record
ord-69f4d2afe8434b96ae98abb8ad45137e
Source dataset
uspto-grants-2010_01
Patent number
US07641915B2

Reaction notes

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