Benzylamine → HCID 4721379, compound

HRID 1944234Notes

Reaction equation

HRID 1944234 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][C:18]=1[O:25][CH3:26])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(Cl)(Cl)Cl>[CH2:1]([NH:8][CH2:21][C:20]1[CH:23]=[CH:24][C:17]([O:16][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[C:18]([O:25][CH3:26])[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 755064-(Benzyloxy)-3-methoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 4721379HCID 4721379, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of benzylamine (13.1 mL, 0.12 mol) and 4-benzyloxy-3-methoxybenzaldehyde (24.2 g, 0.1 mol) in 1,2-dichloroethane (50 mL) and chloroform (250 mL) was added sodium triacetoxyborohydride (31.79 g, 0.15 mol). The mixture was stirred at room temperature for 18 hrs, saturated NaHCO3 was added. The organic phase was separated and aqueous phase extracted with chloroform. The combined extracts were washed with brine, dried over MgSO4 and evaporated to afford the crude product. Purification by flash column chromatography afforded the title compound as a pale yellow oil in 76% yield (25.2 g). Rf: 0.17 (petrol:ethyl acetate; 1:1). 1H NMR (270 MHz, CDCl3) δ 3.73 (2H, s), 3.79 (2H, s), 3.89 (3H, s), 5.13 (2H, s), 6.75-6.84 (2H, m), 6.91 (1H, d, J=1.4), 7.23-7.44 (10H, m); HRMS (ESI+) calcd. for C22H24NO2 (M++H) 334.1802, found 334.1787; LC/MS (ES+) tr=1.19 min, m/z 334.5 (M++H);

Workup

  1. customThe organic phase was separated
  2. extractionaqueous phase extracted with chloroform
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto afford the crude product
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-aae1d76ae6e4437daef43c1478ebd472
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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