Acetic Acid → Ammonia methanol dichloromethane

HRID 33700Notes

Reaction equation

HRID 33700 reaction equation
Cl.[N:2]1([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:50][CH:51]([Cl:53])C>>[NH3:2].[CH3:10][OH:11].[Cl:50][CH2:51][Cl:53].[CH2:24]([N:21]1[CH2:20][CH2:19][N:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][CH2:8][N:2]3[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]3)=[CH:13][CH:14]=2)[CH2:23][CH2:22]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 99240121-[4-(3-Piperidin-1-yl-propoxy)-phenyl]-piperazine hydrochloride

Product 2

HCID 101111911-Benzyl-4-[4-(3-piperidin-1-yl-propoxy)-phenyl]-piperazineHCID 21584172Ammonia methanol dichloromethaneYield 5%

Procedure

A solution of the product of Example 25 (151 mg), benzaldehyde (54 mg), and acetic acid (24 mg) in dichloroethane (3 mL) was treated with sodium triacetoxyborohydride (119 mg). After 14 h, the reaction was quenched with saturated aqueous sodium bicarbonate, and the aqueous phase was extracted with dichloromethane (120 mL). The organic phase was dried (magnesium sulfate) and evaporated in vacuo. Silica gel chromatography of the residue (5% 2M ammonia-methanol/dichloromethane) gave the title compound as an ivory solid (73 mg). 1H NMR (400 MHz, CDCl3): 7.36-7.24 (m, 5H), 6.89-6.80 (m, 4H), 3.94 (t, J=6.4 Hz, 2H), 3.56 (s, 2H), 3.08 (t, J=4.9 Hz, 4H), 2.61 (t, J=5.0 Hz, 4H), 2.48-2.44 (m, 2H), 2.39 (bs, 4H), 1.98-1.91 (m, 2H), 1.61-1.56 (m, 4H), 1.46-1.40 (m, 2H).

Workup

  1. customthe reaction was quenched with saturated aqueous sodium bicarbonate
  2. extractionthe aqueous phase was extracted with dichloromethane (120 mL)
  3. dry with materialThe organic phase was dried (magnesium sulfate)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-0e86a1e79ddf41149078c1f9136e9e56
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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