Formaldehyde → HCID 22342960, compound

HRID 584251Notes

Reaction equation

HRID 584251 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][C:19]2([CH3:25])[CH3:24])[CH2:10][CH:9]1[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][CH3:34])[CH:28]=1)=[O:7].C=O.[C:46](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[Cl:65]CCl>C(O)(=O)C>[ClH:65].[ClH:65].[ClH:65].[F:43][C:2]([F:1])([F:42])[C:3]1[CH:4]=[C:5]([CH:35]=[C:36]([C:38]([F:39])([F:40])[F:41])[CH:37]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][C:19]2([CH3:24])[CH3:25])[CH2:10][CH:9]1[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([N:33]([CH3:46])[CH3:34])[CH:28]=1)=[O:7]

Participants

7

Reactant 5

HCID 712Formaldehyde2×HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 22342675HCID 22342675, compound

Product 1

HCID 22342960HCID 22342960, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A suspension of 1-[3,5-bis(trifluoromethyl)benzoyl]-4-[4-(3,3-dimethylmorpholino)-2-butynyl]-2-[3-(N-methylamino)benzyl]piperazine (0.19 g), 37% aqueous formaldehyde (50 μl), sodium triacetoxyborohydride (79 mg) and acetic acid (22 μl) in dichloromethane (5 ml) was stirred for 2 hours at room temperature. Then additional 37% aqueous formaldehyde (25 μl), acetic acid (10 μl) and sodium triacetoxyborohydride (40 mg) were added to the reaction mixture and the whole was stirred for further 1 hour. The mixture was poured into aqueous saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The extract was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of dichloromethane and methanol (40:1). The fractions containing the objective compound were collected and evaporated under reduced pressure and treated with 4N hydrogen chloride in ethyl acetate solution to give 1-[3,5-bis(trifluoromethyl)benzoyl]-2-[3-(N,N-dimethylamino)benzyl]-4-[4-(3,3-dimethylmorpholino)-2-butynyl]piperazine trihydrochloride (0.21 g).

Workup

  1. stirringthe whole was stirred for further 1 hour
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract was dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using
  6. additiona mixture of dichloromethane and methanol (40:1)
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure
  10. additiontreated with 4N hydrogen chloride in ethyl acetate solution

Sources & evidence

ORD record
ord-df2e78d7038d4d56bc2731c7db6b43fc
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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