Diisopropylethylamine → 3-{4-[(7-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-butyl}-[1,3]oxazinan-2-one

HRID 2301396Notes

Reaction equation

HRID 2301396 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([NH:13][CH2:14][CH2:15][CH3:16])[CH2:10]2)=[CH:5][CH:4]=1.[O:17]=[C:18]1[N:23]([CH2:24][CH2:25][CH2:26][CH:27]=O)[CH2:22][CH2:21][CH2:20][O:19]1.C(N(C(C)C)CC)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:13]([CH2:14][CH2:15][CH3:16])[CH2:27][CH2:26][CH2:25][CH2:24][N:23]3[CH2:22][CH2:21][CH2:20][O:19][C:18]3=[O:17])[CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 100821727-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amineHCID 159226964-(2-Oxo-[1,3]oxazinan-3-yl)butyraldehyde

Product 1

HCID 159226973-{4-[(7-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-butyl}-[1,3]oxazinan-2-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To (7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine (ca. 13 mg 50 umole), was added 440 μL solution of 4-(2-oxo-[1,3]oxazinan-3-yl)-butyraldehyde (0.125 M in 1,2 dichloroethane), 30 μL diisopropylethylamine (DIEA) and 300 μL of 0.25 M slurry of sodium triacetoxyborohydride in 1,2 dichloroethane. The reaction was shaken at room temperature for 48 h. After quenching with 2 mL 2% NaOH, the reaction mixture was transferred along with 0.5 mL water and ethyl acetate to workup flasks. The organic phase was washed, dried and concentrated. Purification by chromatography yielded 3-{4-[(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-butyl}-[1,3]oxazinan-2-one 19, MS: 375 ([M+H]+).

Workup

  1. customAfter quenching with 2 mL 2% NaOH
  2. washThe organic phase was washed
  3. customdried
  4. concentrationconcentrated
  5. customPurification by chromatography

Sources & evidence

ORD record
ord-7f93c167f8834b718aaeda04e658eaf7
Source dataset
uspto-grants-2002_12
Patent number
US06500822B2

Reaction notes

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