Formaldehyde → HCID 10450603, compound

HRID 723311Notes

Reaction equation

HRID 723311 reaction equation
[CH2:1]([N:8]1[C:13]2[CH:14]=[C:15]([CH3:24])[CH:16]=[C:17]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:12]=2[O:11][CH2:10][C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:30](C)=O.[Na+]>C(Cl)Cl>[CH2:1]([N:8]1[C:13]2[CH:14]=[C:15]([CH3:24])[CH:16]=[C:17]([N:18]3[CH2:19][CH2:20][N:21]([CH3:30])[CH2:22][CH2:23]3)[C:12]=2[O:11][CH2:10][C:9]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 10065666HCID 10065666, compound

Product 1

HCID 10450603HCID 10450603, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-Benzyl-6-methyl-8-piperazin-1-yl-4H-benzo[1,4]oxazin-3-one (140 mg, 0.42 mmol) in CH2Cl2 (5 ml) from Example 1 was added formaldehyde (37 wt % solution in water, 50 μl, 0.67 mmol) and NaBH(OAc)3. The solution was stirred with a magnetic stirrer at room temperature for 2 hours, and then partitioned between CH2Cl2 (20 ml) and saturated NaHCO3 solution (20 ml). The aqueous layer was extracted with CH2Cl2 (2×20 ml). After drying over MgSO4, the organic fraction was concentrated in vacuo to give 4-Benzyl-6-methyl-8-(4-methyl-piperazin-1-yl)-4H-benzo[1,4]oxazin-3-one as yellow solid. (140 mg, 95%) MS: (M+H)+352.

Workup

  1. custompartitioned between CH2Cl2 (20 ml) and saturated NaHCO3 solution (20 ml)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×20 ml)
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe organic fraction was concentrated in vacuo

Sources & evidence

ORD record
ord-156c23fa6e284d8ca607c6e30cdc476a
Source dataset
uspto-grants-2006_11
Patent number
US07141562B2

Reaction notes

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