Acetic Acid → Ammonium Hydroxide

HRID 1292382Notes

Reaction equation

HRID 1292382 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.C=O.[C:34](O)(=O)C.C([BH3-])#N.[Na+]>O>[OH-:31].[NH4+:10].[CH3:8][C:6]1[CH:5]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][N:20]([CH3:34])[CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 9979079HCID 9979079, compound

Product 2

HCID 14923Ammonium HydroxideHCID 86752672HCID 86752672, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-[4-[[2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]amino]butyl]phenol (19 mg in 1 mL methanol) was added 0.020 mL of a 37% solution of formaldehyde in water followed by 0.010 mL acetic acid and 16 mg of sodium cyanoborohydride and the mixture stirred at room temperature. After 26 hours the reaction was quenched by the addition of acetic acid, concentrated in vacuo and the excess acetic acid removed by toluene azeotrope. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol, 93.5:6.5; then methylene chloride:methanol:ammonium hydroxide, 90:10:1) gave the title compound (20 mg). m/e=427 (M+H)

Workup

  1. customAfter 26 hours the reaction was quenched by the addition of acetic acid
  2. concentrationconcentrated in vacuo
  3. customthe excess acetic acid removed by toluene azeotrope
  4. customPurification of the
  5. concentrationconcentrate by flash chromatography on silica gel (methylene chloride

Sources & evidence

ORD record
ord-5c6c1cbd41a04ee8a3fea5a060641ed3
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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