Ammonia → HCID 23642206, compound

HRID 750417Notes

Reaction equation

HRID 750417 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]/[CH:44]=[CH: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]/[CH:16]=[CH: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].ClCCl>[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]/[CH:44]=[CH: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]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:25]=1)[CH3:4]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 10473Dimethylamine, hydrochlorideHCID 4311764Sodium borohydrideHCID 86608587HCID 86608587, compound

Product 1

HCID 23642206HCID 23642206, compoundYield 74.4%

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

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-dilinoleyloxybenzaldehyde (6.35 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. 6N Aqueous ammonia (30 mL), was added slowly to the reaction mixture followed by dichloromethane. The reaction mixture was filtered. 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 4.94 g (74%) of a yellow oil.

Workup

  1. stirringto stir at room temperature overnight
  2. filtrationThe reaction mixture was filtered
  3. dry with materialThe filtrate was dried over K2CO3
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant oil was purified via flash chromatography (2-10% acetone in dichloromethane, 0.5% TEA gradient)

Sources & evidence

ORD record
ord-d9e7f6de65c4453a86dc96ca2135efe2
Source dataset
uspto-grants-2008_07
Patent number
US07404969B2

Reaction notes

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