Chloroacetaldehyde → HCID 54557735, compound

HRID 380705Notes

Reaction equation

HRID 380705 reaction equation
[NH2:1][C:2]1[C:3]([Cl:22])=[C:4]([CH:19]=[CH:20][CH:21]=1)[C:5]([NH:7][CH2:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2)=[O:6].[Cl:23][CH2:24][CH:25]=O.C([BH3-])#N.[Na+].Cl>O.CO>[Cl:22][C:3]1[C:2]([NH:1][CH2:25][CH2:24][Cl:23])=[CH:21][CH:20]=[CH:19][C:4]=1[C:5]([NH:7][CH2:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2)=[O:6]

Participants

7

Reactant 4

HCID 33ChloroacetaldehydeHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 20670051HCID 20670051, compound

Product 1

HCID 54557735HCID 54557735, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Prepared according to the method described in Example 63 from 3- amino-2-chloro-N-(tricyclo[3.3.13,7]dec-1-yl)methylbenzamide from Example 54(0.7 g), 50% chloroacetaldehyde in water (0.353 ml), sodium cyanoborohydride (0.159 g), 50% hydrochloric acid in methanol (0.385 ml) and methanol (10 ml), giving the subtitled compound as a white solid (0.777 g) after purification by flash column chromatography eluting with 3:1 iso-hexane:ethylacetate.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0aa4451654d6460d8b17387ba6916c6e
Source dataset
uspto-grants-2001_10
Patent number
US06303659B2

Reaction notes

Loading…