Acetic Acid → HCID 10155518, compound

HRID 1179056Notes

Reaction equation

HRID 1179056 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][NH2:11])=[CH:2]1.[CH2:12]([C:19]1([N:26]([CH3:28])[CH3:27])[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O>[CH2:12]([C:19]1([N:26]([CH3:27])[CH3:28])[CH2:24][CH2:23][CH:22]([NH:11][CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 4721071H-Indol-3-YlmethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 204534784-Benzyl-4-(dimethylamino)cyclohexanone

Product 1

HCID 10155518HCID 10155518, compoundYield 32.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

292 mg C-(1H-Indol-3-yl)-methylamine were partly dissolved in dry 1,2-dichloroethane (10 ml) under argon. After addition of 463 mg 4-benzyl-4-dimethylamino-cyclohexanone (see example 3), glacial acetic acid (4 mmol) and sodium triacetoxyborohydride (550 mg), the suspension was stirred for 72 hours at room temperature. For working up, water (10 ml) was added to the reaction mixture. The organic phase was separated off and the aqueous phase was extracted twice with ether and then rendered strongly alkaline with sodium hydroxide solution. It was extracted again with ethyl acetate (4×10 ml). A pale precipitate precipitated out of the combined ethyl acetate phases even during the processing. After cooling, this was filtered off with suction, washed twice with cold ethyl acetate and dried. 235 mg 1-benzyl-N′-(1H-indol-3-ylmethyl)-N,N-dimethyl-cyclohexane-1,4-diamine were obtained as a cis/trans mixture (m.p. 194-198° C.).

Workup

  1. customThe organic phase was separated off
  2. extractionthe aqueous phase was extracted twice with ether
  3. extractionIt was extracted again with ethyl acetate (4×10 ml)
  4. customA pale precipitate precipitated out of the combined ethyl acetate phases even during the processing
  5. temperatureAfter cooling
  6. filtrationthis was filtered off with suction
  7. washwashed twice with cold ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-7b3481cb340e40d5a1660c79764dd3d0
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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