Formaldehyde → HCID 68936514, compound

HRID 660026Notes

Reaction equation

HRID 660026 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[CH2:11][CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:24](C)=O.[Na+]>ClC(Cl)C>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[CH2:11][CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16][N:17]([CH3:24])[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68935561HCID 68935561, compound

Product 1

HCID 68936514HCID 68936514, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a mixture of 4-methyl-1-(3-piperidin-4-yl-propyl)-2,3-dihydro-1H-indole (1.50 g, 5.81 mmol) in dichloroethane (20 mL) was added formaldehyde (37% in water; 4.0 mL) and Na(OAc)3BH (6.39 g, 30.1 mmol). After 1 h, the mixture was quenched with satd. aq. NaHCO3 and extracted with CHCl3. The organic layer was dried (Na2SO4) and concentrated to obtain the crude residue, which was purified by FCC to give 1.03 g (66%). MS: mass calcd. for C18H28FN5, 272.23; m/z found, 273.4 [M+H]+. 1H NMR (CDCl3): 6.97 (t, J=7.7, 1H), 6.47 (d, J=7.6, 1H), 6.29 (d, J=7.8, 1H), 3.33 (t, J=8.4, 2H), 3.01 (m, 2H), 2.91-2.81 (m, 4H), 2.26 (s, 3H), 2.19 (s, 3H), 1.95-1.86 (m, 2H), 1.74-1.53 (m, 4H), 1.37-1.16 (m, 5H).

Workup

  1. customthe mixture was quenched with satd
  2. extractionaq. NaHCO3 and extracted with CHCl3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dabaf468fda640acac3c2b571f86b0ba
Source dataset
uspto-grants-2011_12
Patent number
US08084466B2

Reaction notes

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