Acetic Acid → HCID 21914447, compound

HRID 1466348Notes

Reaction equation

HRID 1466348 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH2:10]1[CH2:16][O:15][CH2:14][CH2:13][NH:12][CH2:11]1.Cl.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:12]2[CH2:11][CH2:10][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 707414-BromobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 230902141,4-Oxazepane hydrochloride

Product 1

HCID 21914447HCID 21914447, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 4-bromobenzaldehyde (616 mg, 3.3 mmol) in dichloroethane (50 mL) was added homomorpholine hydrochloride (548 mg, 4 mmol) and acetic acid (0.1 mL). Sodium triacetoxyborohydride (3.4 g, 16 mmol) was added and the reaction was stirred overnight. The reaction was quenched with sat. NH4Cl (30 mL). Ethyl acetate (250 mL) was added and the solution was washed with sat. NaHCO3 (2×50 mL), brine (50 mL), dried over MgSO4 and concentrated to dryness. The residue was flushed through a silica plug with (5% MeOH/CH2Cl2) to give a white solid (850 mg, 85%). 1H NMR (400 MHz, CDCl3) δ 7.28 (d, J=7.3 Hz, 2H), 7.10 (d, J=7.3 Hz, 2H), 3.66-3.57 (m, 2H), 3.55-3.50 (m, 2H), 3.46-3.42 (m, 2H), 3.16-3.10 (m, 2H), 2.55-2.45 (m, 4H), 1.75-1.65 (m, 2H).

Workup

  1. customThe reaction was quenched with sat. NH4Cl (30 mL)
  2. additionEthyl acetate (250 mL) was added
  3. washthe solution was washed with sat. NaHCO3 (2×50 mL), brine (50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness
  6. customThe residue was flushed through a silica plug with (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9f76f5b826c543728e3807718b8cdaef
Source dataset
uspto-grants-2015_04
Patent number
US08999968B2

Reaction notes

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